View source for Grigor Dimitrov

{{Short description|Bulgarian tennis player (born 1991)}}
{{Family name hatnote|Dimitrov|Dimitrov|Dimitrov|lang=Bulgarian}}
{{Use dmy dates|date=January 2025}}
{{Infobox tennis biography
|name                            = Grigor Dimitrov<br /> {{Nobold|Григор Димитров}}
|native_name                  = Григор Димитров Димитров
|image                           = [[file:Grigor Dimitrov (2023 DC Open) 01.jpg|frameless|upright=.8]]
|caption                         = Dimitrov in [[2023 Mubadala Citi DC Open|2023 Washington Open]]
|country                         = {{BUL}}
|residence                      = [[Monte Carlo]], Monaco
|birth_date                      = {{Birth date and age|df=yes|1991|05|16}}<ref name="ATP_overview">{{cite web |title=Grigor Dimitrov Overview |url=https://www.atptour.com/en/players/-/D875/overview |website=ATP Tour |publisher=ATP Tour, Inc. |access-date=28 September 2020}}</ref>
|birth_place                    = [[Haskovo]], Bulgaria
|height                           = 1.91m
|turnedpro                      = May 2007
|plays                            = Right (one-handed backhand)
|coach                           = [[Daniel Vallverdu]],<br>[[Jamie Delgado]]
|careerprizemoney          = US$ 30,056,134 <ref name="career-prize-money-leaders">{{cite web|title=ATP Prize Money Leaders |url=http://www.protennislive.com/posting/ramr/career_prize.pdf}}</ref>
*&nbsp;[[Open Era tennis records – Men's singles#Prize money|16th&nbsp;all-time&nbsp;in&nbsp;earnings]] <ref>{{cite web |title=Grigor Dimitrov|url=https://www.atptour.com/en/players/grigor-dimitrov/d875/overview}}</ref>

|singlesrecord                = {{tennis record|won=473|lost=301}}
|singlestitles                  = 9
|highestsinglesranking    = No. 3 (20 November 2017)
|currentsinglesranking     = No. 21 (23 June 2025) <!-- ONLY UPDATE WITH LAST DATE THIS RANKING WAS HELD, NEVER UPDATE UNTIL THE ATP WEBSITE IS UPDATED (ONLY on Mondays) --><ref>{{cite web |title=Grigor Dimitrov Rankings History |url=https://www.atptour.com/en/players/grigor-dimitrov/d875/rankings-history |website=ATP Tour |publisher=ATP Tour, Inc. |access-date=16 February 2021}}</ref>

|AustralianOpenresult     = SF ([[2017 Australian Open – Men's singles|2017]])
|FrenchOpenresult          = QF ([[2024 French Open – Men's singles|2024]])
|Wimbledonresult           = SF ([[2014 Wimbledon Championships – Men's singles|2014]])
|USOpenresult               = SF ([[2019 US Open – Men's singles|2019]])
|Othertournaments         = yes
|MastersCupresult          = '''W''' ([[2017 ATP Finals – Singles|2017]])
|Olympicsresult              = 2R ([[Tennis at the 2012 Summer Olympics – Men's singles|2012]])

|doublesrecord                         = {{tennis record|won=56|lost=78}}
|doublestitles                           = 0
|highestdoublesranking             = No. 66 (26 August 2013)
|currentdoublesranking              = 

|AustralianOpenDoublesresult   = 3R ([[2013 Australian Open – Men's doubles|2013]])
|FrenchOpenDoublesresult        = 2R ([[2013 French Open – Men's doubles|2013]])
|WimbledonDoublesresult         = 2R ([[2011 Wimbledon Championships – Men's doubles|2011]], [[2013 Wimbledon Championships – Men's doubles|2013]])
|USOpenDoublesresult             = 1R ([[2011 US Open – Men's doubles|2011]])
|Mixed                                    = yes
|mixedrecord                           = {{tennis record|won=3|lost=1}}
|AustralianOpenMixedresult      =
|FrenchOpenMixedresult          = 1R ([[2011 French Open – Mixed doubles|2011]])
|WimbledonMixedresult           =
|USOpenMixedresult               =
|Team                                    = yes
|DavisCupresult                      = 20–4
|HopmanCupresult                  = RR ([[2012 Hopman Cup|2012]])
|updated                                = 23 June 2025
}}

'''Grigor Dimitrov Dimitrov''' ({{langx|bg|Григор Димитров Димитров}}, {{IPA|bg|ɡriˈɡɔr dimiˈtrɔf|pron}}; born 16 May 1991) is a Bulgarian professional [[tennis]] player. He has been [[ATP rankings|ranked]] as high as world No. 3 in singles by the [[Association of Tennis Professionals|ATP]], making him the highest-ranked Bulgarian in history. Dimitrov reached the ranking after winning the biggest title of his career at the season-ending [[2017 ATP Finals – Singles|ATP Finals]] in November 2017. He has won nine [[ATP Tour]] singles titles.

Prior to his professional career, Dimitrov enjoyed a successful junior career, in which he reached the world No. 1 ranking and won consecutive [[Grand Slam (tennis)#Tournaments|major]] boys' singles titles at the [[2008 Wimbledon Championships – Boys' singles|2008 Wimbledon Championships]] and the [[2008 US Open – Boys' singles|2008 US Open]]. In October 2013 at the [[2013 If Stockholm Open – Singles|Stockholm Open]], Dimitrov became the first Bulgarian man to win an ATP Tour singles title. As of 2025, he is the male player with the longest active streak of [[All-time tennis records – men's singles#Grand Slam tournaments consecutive streaks|consecutive Grand Slam]] appearances, at 58.<ref>{{cite web | url=https://www.atptour.com/en/news/roland-garros-2022-tuesday-qualifying | title=Feliciano Lopez Falls in Roland Garros Qualifying as Grand Slam Streak Ends |website=ATP Tour}}</ref><ref>{{cite tweet|number=1526578076083228673|user=ITFMedia|title=@rolandgarros The player with the longest active streak of Grand Slam men's singles main draw appearances is now…|date=17 May 2022}}</ref> By reaching the [[2024 French Open]] quarterfinals, Dimitrov became the second player born in the 1990s (after [[Daniil Medvedev]]), to complete the career set of both Grand Slam and Masters 1000 quarterfinals.<ref name=CareerSetQF>{{cite web|title=Grigor Dimitrov completes career set of Grand Slam quarterfinals at Roland Garros|url=https://www.tennis.com/news/articles/grigor-dimitrov-completes-career-set-of-grand-slam-quarterfinals-at-roland-garros|date=2 June 2024|accessdate=2 June 2024|website=Tennis.com}}</ref>

Dimitrov was named [[Bulgarian Sportsperson of the Year]] in 2014 and 2017, marking the first and second occasions a tennis player received the honor since the award's inception in 1958. In 2017, he was also awarded the [[BTA Best Balkan Athlete of the Year|Balkan Athlete of the Year]].<ref name="reuters1">{{cite news | title = Dimitrov beats Halep to win Balkan athlete of year|publisher=Reuters|date=18 December 2017|url= https://www.yahoo.com/news/dimitrov-beats-halep-win-balkan-athlete-121432410--sow.html}}</ref><ref name="autogenerated1">{{Cite web|title=Grigor Dimitrov voted Balkan Athlete of 2017|url=https://bnr.bg/en/post/100910329/grigor-dimitrov-voted-balkan-athlete-of-2017|access-date=2021-11-23|website=bnr.bg}}</ref><ref>{{cite web|url=https://www.bta.bg/bg/news/sport/bg/816349-vsichki-pobediteli-v-anketata-na-bta-sportist-na-balkanite-|title= Всички победители в анкетата на БТА "Спортист на Балканите"|date=January 17, 2025 |publisher=www.bta.bg|author=Dimitar Veliov |access-date=May 16, 2025}}</ref> In December 2024, he was selected the winner of the [[ATP Awards#Stefan Edberg Sportsmanship Award|Stefan Edberg Sportsmanship Award]].<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-atp-awards-2024-stefan-edberg-sportsmanship-award|title= Dimitrov wins 2024 Stefan Edberg Sportsmanship Award|date=13 December 2024|website=ATPTour}}</ref>
{{TOC limit|2}}

==Early life==
Grigor Dimitrov was born in [[Haskovo]] to father Dimitar Dimitrov, a tennis coach, and mother Maria Dimitrova, a sports teacher and former volleyball player, in 1991.<ref name="ATP_bio">{{cite web |title=Grigor Dimitrov Bio |url=https://www.atptour.com/en/players/grigor-dimitrov/d875/bio |website=ATP Tour |publisher=ATP Tour, Inc. |access-date=28 October 2019}}</ref> He first held a tennis racket, given to him by his mother, at the age of three,<ref name="ATP_bio"/> and when he was five he began to play daily. In his early years his father served as his coach, but after he proved his talent in the tournaments for juniors, he made it clear that he would have to develop in other conditions. At the age of 16, Dimitrov turned professional.

In 2007, Dimitrov joined the academy "Sanchez-Casal", where he was further trained under the leadership of [[Emilio Sánchez]] and [[William Álvarez (tennis)|Pato Álvarez]]. Since March 2009 Dimitrov trained in [[Paris]], France, where he joined [[Patrick Mouratoglou]]'s [[Mouratoglou Tennis Academy|tennis academy]] and spent the next four seasons there and he appointed Patrick Mouratoglou as coach for 2012.<ref>{{cite web|title=Moratoglou academy and coaching|date=8 November 2018|url=https://www.tennishead.net/dimitrov-appoints-mouratoglou-as-coach}}</ref>

==Personal life==
Dimitrov began dating [[Maria Sharapova]] in late 2012. He and Sharapova only confirmed their relationship after the [[2013 Mutua Madrid Open|2013 Madrid Open]] where the Bulgarian managed his first win against a world No. 1, beating [[Novak Djokovic]].<ref>{{cite web |title=Sharapova, Dimitrov linked again|url=http://www.tennis.com/your-game/2013/01/sharapova-dimitrov-linked-again/45899/ |access-date=7 January 2013}}</ref> Sharapova and Dimitrov separated in July 2015.<ref>{{cite news|last=Chase|first=Chris|title=Maria Sharapova splits with Grigor Dimitrov|work=USA Today|date=July 27, 2015|access-date=21 October 2021|url=https://ftw.usatoday.com/2015/07/maria-sharapova-grigor-dimitrov-break-up-split-boyfriend-dating}}</ref> At the end of 2015, he started discreetly dating American singer [[Nicole Scherzinger]], the lead vocalist of [[The Pussycat Dolls]].<ref>{{cite web |title=nicole scherzinger dating tennis star grigor dimitrov |date=18 November 2015|url=https://www.toronto.com/whatson-story/6123126-nicole-scherzinger-dating-tennis-star-grigor-dimitrov/}}</ref> Their romantic relationship ended in 2019. Since then, he has been involved in relationships with businesswoman Lolita Osmanova, president of the ''Luxury International'' magazine, as well as Romanian actress [[Mădălina Ghenea]]. Since April 2025, Dimitrov is in a relationship with Mexican actress [[Eiza González]], confirmed through an [[Instagram]] post.<ref>{{cite web|url=https://www.tennis.com/baseline/articles/eiza-gonzalez-man-my-dreams-grigor-dimitrov-relationship-confirmed|title=Eiza González recognizes "man of my dreams" Grigor Dimitrov in glowing birthday tribute|publisher=Tennis.com|language=EN|date=May 16, 2025|access-date= May 17, 2025}}</ref>

In addition to his native Bulgarian, he speaks English and says his main interests are sports, cars, computers and watches.<ref>{{cite web |title=10 things you didn't know about grigor dimitrov|date=17 December 2017|url=https://www.essentiallysports.com/10-things-didnt-know-grigor-dimitrov/}}</ref> Early in his career he was given the nickname "Baby Fed" for his stylish play and on-court talent being similar to that of [[Roger Federer]].<ref>{{cite web |last=Cronin |first=Matt |title=FEDERER: GET RID OF 'BABY FED' NICKNAME FOR DIMITROV |url=http://www.tennis.com/pro-game/2013/10/federer-get-rid-baby-fed-nickname-dimitrov/49585/ |publisher=Tennis |date=26 October 2013 |access-date=3 August 2016}}</ref>

==Junior career==
He claimed his first major junior cup, the U14 European title, at the age of 14.<ref>{{cite web|title=Dimitrov Junior Career| date=17 December 2017| url=https://www.essentiallysports.com/10-things-didnt-know-grigor-dimitrov}}</ref> In 2006, he won the [[Dunlop Orange Bowl|Orange Bowl]] U16 boys singles<ref>[http://www.usta.com/Archive/News/Juniors/Junior/385580_Will_Captures_Orange_Bowl_16s_Singles_Title/ Will Captures Orange Bowl 16s Singles Title] {{Webarchive|url=https://web.archive.org/web/20160811085805/https://www.usta.com/Archive/News/Juniors/Junior/385580_Will_Captures_Orange_Bowl_16s_Singles_Title/ |date=11 August 2016 }}. United States Tennis Association. 25 May 2008</ref> and was later named the Eddie Herr International 2007 Rising Star.<ref>[http://www.eddieherr.com/index.htm Eddie Herr International Junior Tennis Championships] {{Webarchive|url=https://web.archive.org/web/20111116004421/http://www.eddieherr.com/index.htm |date=16 November 2011}}. Eddieherr.com. Retrieved on 11 October 2011.</ref>

In 2007, Dimitrov was the finalist at the [[Dunlop Orange Bowl|Orange Bowl]] U18 boys singles losing to [[Ričardas Berankis]] of [[Lithuania]]. With [[Vasek Pospisil]], he reached the [[2007 US Open – Boys' doubles|US Open]] doubles final falling to [[Jonathan Eysseric]] and [[Jérôme Inzerillo]].
[[File:Grigor Dimitrov.jpg|right|thumb|upright=.7|Dimitrov as junior Wimbledon champion for 2008]]
He began the 2008 [[Grand Slam (tennis)|Grand Slam]] season with a quarterfinal showing at the [[2008 French Open – Boys' singles|French Open]], losing to Poland's [[Jerzy Janowicz]] in three sets. However he went on to win [[2008 Wimbledon Championships – Boys' singles|Wimbledon]] after defeating [[Henri Kontinen]] of Finland in the final. He won the title without dropping a set despite playing with a shoulder injury throughout the tournament. The victory saw him join former junior champions [[Roger Federer]] and [[Stefan Edberg]] and guaranteed him a wildcard entry into the 2009 Wimbledon men's draw. His success continued at the [[2008 US Open – Boys' singles|US Open]], which he won on 7 September, defeating American qualifier [[Devin Britton]] in two sets.<ref>{{cite news|url=http://sportal.bg/news.php?id=130158|title=Блестящ Григор Димитров спечели и US Open|date=7 September 2008|access-date=7 September 2008|publisher=[[sportal.bg]]|language=bg }}</ref> On his way to the title he also defeated top seed [[Yang Tsung-hua]] of Taiwan in the semifinals. After the tournament Dimitrov announced that he was ending his junior career and focusing on improving his [[ATP ranking]].<ref>{{Cite web|url=http://tenniskalamazoo.blogspot.com/2008/09/vandeweghe-wins-first-title-dimitrov.html|title=Vandeweghe Wins First Title, Dimitrov Ends Junior Career with Second Straight Slam|accessdate=26 June 2023}}</ref> On 8 September 2008, he became junior world No. 1 overtaking Yang Tsung-hua.<ref>{{cite web|url=https://www.itftennis.com/en/rankings/world-tennis-tour-junior-rankings|title=ITF Junior Rankings|date=8 September 2008|access-date=8 September 2008|publisher=www.itftennis.com/en/itf-tours/world-tennis-tour-juniors}}</ref> He closed at No. 3 of the junior ranking that year.<ref>{{cite web| title=2008 Juniors Year-End ITF rankings|url=http://www.collegeandjuniortennis.com/ITFRank08/Final08Boys.htm}}</ref> Dimitrov compiled a singles win–loss record of 74–28 as a junior (and 42–20 in doubles).<ref>{{cite web|title=Dimitrov junior career statistics|url= https://www.itftennis.com/en/players/grigor-dimitrov/800263094/bul/jt/s/overview/}}</ref>

<u>Junior Grand Slam performance – Singles:</u>

Australian Open: A (-)<br />
French Open: QF ([[2008 French Open – Boys' singles|2008]])<br />
Wimbledon: '''W''' ([[2008 Wimbledon Championships – Boys' singles|2008]])<br />
US Open: '''W''' ([[2008 US Open – Boys' singles|2008]])

==Professional career==
===2008: ATP Tour debut===
In 2008, Dimitrov began frequent participation in men's events. His first title came on clay at a futures tournament in Barcelona.
His first ATP level match was at the [[2008 Ordina Open|Rosmalen Open]] where he lost to [[Igor Andreev]] in straight sets. After his junior US Open title he won back to back futures tournaments in Madrid on hardcourt and rose 300 places to career high ranking of 477. The achievement attracted enough attention to earn him a wildcard into the [[2008 Mutua Madrileña Madrid Open|Madrid Open]] qualifying draw where he lost to then-No. 64, [[Florent Serra]] of France. After being granted another wildcard to the [[2008 Davidoff Swiss Indoors|Swiss Indoors]] qualifying draw, he defeated No. 122, [[Jiří Vaněk (tennis)|Jiří Vaněk]], in three sets in the first round for his first ATP level win, before losing to [[Julian Reister]].

===2009: First ATP Tour match win, Grand Slam debut===
In 2009, he was granted a wildcard to the main draw of the [[2009 ABN AMRO World Tennis Tournament – Singles|Rotterdam Open]] and scored an upset over then-world No. 23, [[Tomáš Berdych]], earning his first ATP Tour main-draw win. In the second round, he faced world No. 1, [[Rafael Nadal]], and lost in three sets.

He was granted a wildcard to the main draw of the [[2009 Open 13 – Singles|Open 13]] in Marseille but lost to world No. 8, [[Gilles Simon]], in the first round, despite serving for the match at ninth game of the third set. He then completed two victories in the Davis Cup against Hungary. He lost to [[Danai Udomchoke]] in straight sets in the second round of the [[2009 SAT Bangkok Open|Bangkok Open]]. Four first-round exits in Challengers followed. He then reached the quarterfinals after qualifying of two successive Challengers at the [[2009 Trofeo Paolo Corazzi|Trofeo Paolo Corazzi]] and [[2009 Aegon Trophy|Nottingham Trophy]]. He reached the second round of the [[2009 Aegon Championships|Queen's Club Championships]] after defeating [[Iván Navarro (tennis)|Iván Navarro]], but lost in two tiebreaks to [[Gilles Simon]].

On his Grand Slam debut at the [[2009 Wimbledon|Wimbledon]] where he got a wildcard as the 2008 juniors champion, he won the first set of his first-round match against [[Igor Kunitsyn]] but then suffered a knee injury. Despite this he attempted to continue but lost the following ten games before he retired.

He was granted a wildcard to the main draw of the [[2009 Swedish Open|Swedish Open]] but lost in the first round to [[Guillermo Cañas]]. He reached the quarterfinals of the Challenger [[2009 Open Castilla y León|Open Castilla y León]] losing out in three sets to [[Marcel Granollers]]. He then lost in the second round to [[Martin Fischer (tennis)|Martin Fischer]] in straight sets at the [[2009 American Express – TED Open|Istanbul Challenger]]. As the 2008 winner of the [[US Open (tennis)|US Open]] boys tournament he was granted a wildcard for the [[2009 US Open (tennis)|US Open]] qualification tournament. He won his first-round match against [[Tobias Kamke]] but in the second round lost to the top seed of the qualifying, [[Thomaz Bellucci]]. Dimitrov won his first doubles Challenger title at the [[2009 ATP Challenger Trophy|ATP Challenger Trophy]] with [[Teymuraz Gabashvili]] beating [[Jan Minář]] and [[Lukáš Rosol]]. He then received a wildcard at the [[2009 If Stockholm Open|Stockholm Open]] but lost in the first round to [[Jarkko Nieminen]].

===2010: Top 250 debut, first Challenger title===
Dimitrov started the season with a quarterfinal finish at a Challenger event of [[2010 Internationaux de Nouvelle-Calédonie|Internationaux de Nouvelle-Calédonie]]. He then attempted to qualify for the [[2010 Australian Open|Australian Open]], but lost in the first round to [[Robert Kendrick]] in three sets.[[File:Grigor apano1.png|thumb|left|upright=.7|Dimitrov in 2010]]
He bounced back a week later by qualifying at the [[2010 Honolulu Challenger|Honolulu Challenger]], but lost to [[Donald Young (tennis)|Donald Young]] in the second round. Dimitrov then participated for Bulgaria in the [[Davis Cup]], claiming all three wins in a 3–2 victory over Monaco. Following the Davis Cup tie, Dimitrov had a number of early losses in various Challenger tournaments. 
Dimitrov won his first ATP Tour match of the year on the grass courts of the [[2010 Queen's Club Championships – Singles|Queen's Club]] in London. He beat [[Alex Bogdanovic]] before losing to world No. 31, [[Feliciano López]], in the second round. He then had a great run in the [[2010 Marburg Open – Singles|Marburg Open]], a Challenger event, where he came through qualifying to reach the semifinals where he lost out to [[Simone Vagnozzi]]. Dimitrov again had a number of disappointing losses in Challenger events and another Davis Cup tie. Dimitrov then participated in four futures tournaments, posting impressive results, including two tournament victories in Germany, and another in Spain. Dimitrov gained enough points to enter the world's top 250 for the first time in his career.

His good form translated to the Challenger Tour, capturing three consecutive titles, the first coming at the [[2010 IPP Trophy|Geneva Open Challenger]], defeating [[Pablo Andújar]] in three sets. And back to back titles at the [[2010 Chang-Sat Bangkok Open|Bangkok Open]], where he beat former top 20 player [[Dmitry Tursunov]] in the quarterfinals and [[Konstantin Kravchuk]] in the final, and at the [[2010 Chang-Sat Bangkok Open 2|Bangkok Open 2]] defeating [[Alexander Kudryavtsev]].<ref>{{Cite web|title=First Challenger Title for Grigor Dimitrov :. Grigor Dimitrov|url=https://www.grigor-dimitrov.com/news/show/article/first-challenger-title-for-grigor-dimitrov|access-date=2021-11-23|website=www.grigor-dimitrov.com}}</ref><ref>Lerpong Amsa-ngiam [http://www.nationmultimedia.com/home/2010/09/26/opinion/Game-set-and-match--Grisha%27s-on-the-ball-30138739.html Game, set and match – Grisho's on the ball]{{dead link|date=January 2025|bot=medic}}{{cbignore|bot=medic}}. The Nation. 26 September 2010</ref> He made an early exit in his first Challenger after a two-week break but bounced back a week later, beating top 100 player [[Lukáš Lacko]] and world No. 32 [[Michaël Llodra]] on the way to the final of the [[2010 Open d'Orléans|Open d'Orléans]]. In the final, Dimitrov lost to [[Nicolas Mahut]] in a third set tiebreak. After two disappointing Challenger tournaments in Germany, in which Dimitrov suffered first round exits, he reached the semifinals of [[2010 IPP Open|IPP Open]] in Helsinki, his last tournament of the year. There he played Lithuanian youngster [[Ričardas Berankis]]. After the loss of a tight first set in a tiebreak, Dimitrov dominated the second set but was dominated in turn by Berankis in a third set loss. In an off-court incident after the match, Dimitrov pushed the chair umpire with both hands and swore at him because he felt he was treated unfairly after some close calls in the first set tiebreak. Dimitrov was fined €2,000. By reaching the semifinals in Helsinki, Dimitrov reached his best ever ATP World ranking of No. 106.

===2011: Top 100===
His first tournament of the year was the [[2011 Australian Open – Men's singles|Australian Open]] where he advanced through the [[2011 Australian Open – Men's singles qualifying|qualifying rounds]] with the loss of just one set. He defeated world No. 38, [[Andrey Golubev]], to advance for the first time to the second round of a [[Grand Slam (tennis)|Grand Slam tournament]] where he lost to 19th seed [[Stanislas Wawrinka]]. Nonetheless, Dimitrov achieved his top ever ATP ranking ending January at World No. 85. Thus, he became the top ranked Bulgarian male tennis player of all time.

Dimitrov then qualified for the [[2011 ABN AMRO World Tennis Tournament|Rotterdam Open]] but lost to eighth seed [[Jo-Wilfried Tsonga]] in the first round in two sets.<ref>{{cite web|url=http://tennis.sportal.bg/news.php?news=284017|title=Grigor entered history books|date=31 January 2011|publisher=sportal.bg|access-date=31 January 2011|language=bg|archive-date=4 March 2016|archive-url=https://web.archive.org/web/20160304034705/http://tennis.sportal.bg/news.php?news=284017|url-status=dead}}</ref> He then lost in the first rounds of the [[2011 Open 13|Marseille Open]] and [[2011 Dubai Tennis Championships|Dubai Tennis Championships]] to Dmitry Tursunov and [[Richard Gasquet]], respectively. Dimitrov then won the [[2011 Challenger DCNS de Cherbourg|Challenger de Cherbourg]] defeating defending champion and second seed Nicolas Mahut in the final.

He then qualified for the [[2011 Sony Ericsson Open|Miami Open]] losing to [[Sergiy Stakhovsky]]. Dimitrov became the first Bulgarian man ever to be seeded at an ATP World Tour tournament being seeded eighth at the [[2011 U.S. Men's Clay Court Championships|U.S. Clay Court Championships]] but lost in the second round to [[Teymuraz Gabashvili]]. At the [[2011 Barcelona Open Banco Sabadell|Barcelona Open]], he lost in the first round to [[Juan Mónaco]]. He had reached his first quarterfinal in an ATP tournament at the [[2011 BMW Open|BMW Open]], after defeating [[Marcos Baghdatis]] but then lost to [[Florian Mayer]] in three sets. Dimitrov lost in the first round of the [[2011 French Open|French Open]] to [[Jérémy Chardy]].

Dimitrov then advanced to his second ATP quarterfinals at the [[2011 Aegon International|Eastbourne International]] after he defeated sixth seeded [[Kevin Anderson (tennis)|Kevin Anderson]] in the second round, but lost in the third round to third seed [[Janko Tipsarević]]. He also competed in the doubles with [[Andreas Seppi]] and became the first Bulgarian man ever to reach a doubles final at an ATP tournament, they lost to [[Jonathan Erlich]] and [[Andy Ram]]. At [[2011 Wimbledon|Wimbledon]], he lost a memorable second round match to Jo-Wilfried Tsonga, in a tight four-setter. He then reached the second rounds of the [[2011 Campbell's Hall of Fame Tennis Championships|Hall of Fame Tennis Championships]] and [[2011 Farmers Classic|Farmers Classic]], losing to Americans [[Denis Kudla]] and [[Alex Bogomolov Jr.]] At the [[2011 Atlanta Tennis Championships|Atlanta Tennis Championships]], he fell to [[Rajeev Ram]] in the first round. At the [[2011 Western & Southern Open – Men's singles|Western & Southern Open]] Dimitrov defeated [[Marsel İlhan]] in the first round, but lost to world No. 6, [[David Ferrer]], in the second round in three sets.<ref>{{cite web|url=http://www.dnevnik.bg/sport/2011/08/15/1139560_grigor_dimitrov_specheli_purvata_si_pobeda_v_masturs|title=Григор Димитров спечели първата си победа в "Мастърс" турнир|language=bg|date=15 August 2011|access-date=15 August 2011}}</ref> He also played in the third round of the [[2011 Winston-Salem Open|Winston-Salem Open]] being defeated by [[Alexandr Dolgopolov]] in a third set tie-break. At the [[2011 US Open – Men's singles|US Open]], Dimitrov was defeated by [[Gaël Monfils]] in the first round.<ref>Edward, Neil. (29 August 2011) [http://www.usopen.org/en_US/news/match_reports/2011-08-29/201108301314671946176.html Monfils advances over Dimitrov in style|News and Photos|2011 US Open Official Site – A USTA Event] {{webarchive|url=https://web.archive.org/web/20110913191616/http://www.usopen.org/en_US/news/match_reports/2011-08-29/201108301314671946176.html |date=13 September 2011 }}. US Open. Retrieved on 11 October 2011.</ref> At the [[2011 Open de Moselle|Open de Moselle]], Dimitrov was beaten in 53 minutes by qualifier [[Igor Sijsling]] in the first round.<ref>{{Cite web|date=2011-09-20|title=Sijsling, Paire reach 2nd round at Moselle Open|url=https://www.espn.com/tennis/story/_/id/6996887/igor-sijsling-benoit-paire-reach-2nd-round-moselle-open|access-date=2021-11-23|publisher=ESPN}}</ref> After that, in the [[2011 PTT Thailand Open|Thailand Open]], Dimitrov beat [[Ivan Dodig]] and [[Simone Bolelli]], before falling to [[Andy Murray]] in the quarterfinals in two sets.

In his next tournament, at the [[2011 China Open (tennis)|China Open]], he lost once again to top-seeded Jo-Wilfried Tsonga in the first round. At [[2011 Shanghai Rolex Masters|Shanghai Masters]] Dimitrov beat [[Marsel İlhan]] in the first round but was defeated by Andy Roddick in the second round in two tight sets.<ref>{{cite web|url=http://www.dnes.bg/sport/2011/10/11/grigor-dimitrov-izpusna-andi-rodik.130998|title=Григор Димитров изпусна Анди Родик|language=bg|date=11 October 2011|access-date=16 October 2011}}</ref> At the [[2011 If Stockholm Open – Singles|Stockholm Open]] Dimitrov beat [[Ryan Sweeting]] and [[Juan Ignacio Chela]] before losing to [[Milos Raonic]] in the quarterfinals.<ref>{{cite web|url=http://www.sportni.bg/index.phtml?tid=40&oid=2720919|archive-url=https://archive.today/20120917214607/http://www.sportni.bg/index.phtml?tid=40&oid=2720919|url-status=dead|archive-date=17 September 2012|title=Григор Димитров изпусна полуфинала в Стокхолм|language=bg|date=21 October 2011|access-date=21 October 2011}}</ref> He ended the year ranked No. 76.

===2012: First top 10 win, top 50 year-end===
Dimitrov started his 2012 season by competing at the [[2012 Hopman Cup|Hopman Cup]] alongside [[Tsvetana Pironkova]]. Their team was defeated by the [[Czech Republic at the Hopman Cup|Czech Republic]] 1–2, after they won a match in mixed doubles but lost their singles matches. Then, their team defeated [[Denmark at the Hopman Cup|Denmark]] 2–1.<ref>{{cite web|url=http://www.sportni.bg/index.phtml?tid=40&oid=2724824|title=Гришо и Цвети с победа на двойки срещу чехите|language=bg|date=2 January 2012|access-date=2 January 2012|archive-date=8 January 2012|archive-url=https://web.archive.org/web/20120108013634/http://www.sportni.bg/index.phtml?tid=40&oid=2724824|url-status=dead}}</ref> Against USA, Dimitrov dispatched Mardy Fish in straight sets in his first win (although not official ATP win) against a top 10 player.

At the [[2012 Australian Open – Men's singles|Australian Open]], Dimitrov defeated [[Jérémy Chardy]] to reach the second round but then he lost in five sets to [[Nicolás Almagro]]. Dimitrov competed in the [[2012 SAP Open – Singles|Pacific Coast Championships]] but lost in the first round to Kevin Anderson, despite winning the first set easily, lost the next two in tie-breaks.<ref>{{cite web|url=http://www.sportni.bg/index.phtml?tid=40&oid=2727572|title=Южноафриканец удари Григор Димитров в Сан Хосе|language=bg|date=14 February 2012|access-date=15 February 2012|archive-date=15 February 2012|archive-url=https://web.archive.org/web/20120215124938/http://www.sportni.bg/index.phtml?tid=40&oid=2727572|url-status=dead}}</ref>

At [[2012 BNP Paribas Open – Men's singles|Indian Wells]], Dimitrov defeated [[Ivan Dodig]] in the first round, but lost to David Ferrer in the second round. Dimitrov's next tournament was the [[2012 Sony Ericsson Open – Men's singles|Miami Open]] where he reached the fourth round, after defeating [[Mikhail Kukushkin]], [[Juan Ignacio Chela]], and upsetting world No. 7, Tomáš Berdych, his first win over a top-ten player, before losing to Janko Tipsarević.<ref>{{cite web|url=http://www.sportni.bg/index.phtml?tid=40&oid=2730066|title=Гришо мина и през Чела в Маями|language=bg|date=24 March 2012|access-date=24 March 2012|archive-date=30 June 2012|archive-url=https://web.archive.org/web/20120630062628/http://www.sportni.bg/index.phtml?tid=40&oid=2730066|url-status=dead}}</ref><ref>{{cite web|url=http://www.sonyericssonopen.com/News/Tennis/2012/Tournament/Sunday/ATP-Miami-Sunday-Dimitrov-Upsets-Berdych.aspx|title=Dimitrov upsets Berdych for first top 10 win|date=25 March 2012|access-date=25 March 2012|archive-url=https://web.archive.org/web/20120327161424/http://www.sonyericssonopen.com/News/Tennis/2012/Tournament/Sunday/ATP-Miami-Sunday-Dimitrov-Upsets-Berdych.aspx|archive-date=27 March 2012|url-status=dead}}</ref> Dimitrov entered the Challenger event [[2012 Strabag Prague Open|Prague Open]] as the fifth seeded player. In the first round he defeated [[Jan Hájek (tennis)|Jan Hájek]] and then lost to [[Aljaž Bedene]] in the second. At the [[2012 French Open|French Open]], Dimitrov was a set and a break up against 17th seed [[Richard Gasquet]] before a 38 shot rally left Dimitrov cramping up and Gasquet vomiting, and caused Dimitrov to lose momentum, the set, and eventually the match.<ref>{{cite news |last1=Nguyen |first1=Courtney |title=Watch: Grigor Dimitrov, Richard Gasquet and a 38-shot rally |url=https://www.si.com/tennis/2012/06/01/watch-grigor-dimitrov-and-richard-gasquets-32-shot-rally |access-date=June 9, 2024 |date=June 1, 2012}}</ref>

[[File:Dimitrov 2012 US Open 1.jpg|thumb|upright=.7|left|Dimitrov at the 2012 US Open]]
Dimitrov's next tournament was the [[2012 Aegon Championships – Singles|Birmingham Championships]]. He beat [[Bobby Reynolds]], [[Gilles Müller]] and Nicolas Mahut and then reached his first ATP semifinal by beating the No. 9 seed, Kevin Anderson by coming back from a set down. Dimitrov became the first ever Bulgarian male tennis player to reach an ATP semifinal.<ref>{{cite web|url=http://www.lta.org.uk/fans-major-events/LTA-summer-grass-court-events/AEGON-Championships/News/2012/Grigor-Dimitrov-in-AEGON-Championships-semi-finals|title=Grigor Dimitrov in AEGON Championships semi-finals|date=15 June 2012|access-date=16 June 2012|archive-date=3 December 2013|archive-url=https://web.archive.org/web/20131203053353/http://www.lta.org.uk/fans-major-events/LTA-summer-grass-court-events/AEGON-Championships/News/2012/Grigor-Dimitrov-in-AEGON-Championships-semi-finals/|url-status=dead}}</ref> In his first ATP semifinal, Dimitrov lost to tenth seeded [[David Nalbandian]] in straight sets.<ref>{{cite news |url=https://www.bbc.co.uk/sport/0/tennis/18472872|title=Grigor Dimitrov|publisher=BBC Sport |access-date=17 June 2012}}</ref> This tournament helped him become No. 65 in the rankings.

At the [[2012 Wimbledon Championships]], Dimitrov faced the No. 32 seed, Kevin Anderson in the first round. Dimitrov won in a very close four sets. In the second round, he faced the Cypriot [[Marcos Baghdatis]], where Dimitrov retired due to an injury. His next tournament was [[2012 Swedish Open|Swedish Open]]. Seeded sixth, he eliminated [[Rogério Dutra da Silva]], [[Frederico Gil]], and third seed [[Albert Ramos]] all in straight sets to reach a second ATP semifinal in his career. In the semifinal, he lost to the top seed and eventual champion David Ferrer in straight sets. Dimitrov then competed in the [[2012 Crédit Agricole Suisse Open Gstaad|Suisse Open Gstaad]]. He defeated sixth seed [[Julien Benneteau]], [[Dustin Brown (tennis)|Dustin Brown]], and [[Łukasz Kubot]]. In his third career semifinal, he lost again – this time to Thomaz Bellucci in two tough tiebreaks.

On the grass of Wimbledon, Dimitrov represented his country for the first time in the [[Tennis at the 2012 Summer Olympics|Olympics]]. In the first round, he defeated Pole Łukasz Kubot again in two tight sets, two weeks after he had beaten him in the Swiss Open quarterfinal. He fell in the second round to the 12th seed, Gilles Simon – his fourth loss against Simon (whom he has never beaten).

On hardcourts, Dimitrov has failed to qualify for [[2012 Rogers Cup|Rogers Cup]] and [[2012 Western & Southern Open|Western & Southern Open]]. In both Masters tournaments, he lost in the first round of the qualifying round to [[Marco Chiudinelli]] and [[Rajeev Ram]] respectively. Dimitrov suffered a first lost at the final slam of the year, the [[2012 US Open (tennis)|US Open]] to Benoît Paire in four sets. He ended his drought at the [[2012 PTT Thailand Open|Thailand Open]], reaching the second round before losing to Richard Gasquet in three tight sets. He then qualified for the [[2012 Rakuten Japan Open Tennis Championships|Japan Open]], but fell to Juan Mónaco in straight sets.

At the Masters event of [[2012 Shanghai Rolex Masters|Shanghai]], he defeated [[Pablo Andújar]] before losing to world No. 2 [[Novak Djokovic]]. At the [[2012 Swiss Indoors Basel|Swiss Indoors Basel]] Dimitrov reached the quarterfinals, defeating [[Viktor Troicki]] in straight sets and Julien Benneteau in three tie-break sets, before losing to [[Paul-Henri Mathieu]] in two tie-break sets. His next tournament was the [[2012 BNP Paribas Masters|Paris Masters]], after receiving an entry from the qualifying draw. He beat [[Jürgen Melzer]] before his 2012 campaign ended at the hands of Juan Mónaco.<ref>{{cite web|url=http://www.sportni.bg/index.phtml?tid=40&oid=2741974|title=Григор Димитров срещу Юрген Мелцер в първия кръг в Париж|access-date=29 October 2012|archive-date=31 October 2012|archive-url=https://web.archive.org/web/20121031054038/http://www.sportni.bg/index.phtml?tid=40&oid=2741974|url-status=dead}}</ref> Dimitrov ended 2012 ranked world No. 48 in singles.

===2013: First ATP title===
Dimitrov began his 2013 season by competing at the [[2013 Brisbane International|Brisbane International]]. He defeated [[Brian Baker (tennis)|Brian Baker]], world No. 13 [[Milos Raonic]], Jürgen Melzer, and Marcos Baghdatis to reach his first ATP singles final, thus becoming the first Bulgarian player to reach an ATP final.<ref>{{cite web|title=Incredible Grigor Dimitrov Reaches Brisbane Semi-Finals|url=http://www.novinite.com/view_news.php?id=146552|access-date=4 January 2013}}</ref><ref>{{cite web|title=MURRAY SURVIVES SCARE; DIMITROV SINKS RAONIC|url=http://www.atpworldtour.com/News/Tennis/2013/01/1/Brisbane-Thursday-Dimitrov-Raonic-Hewitt-Murray.aspx|access-date=3 January 2013}}</ref><ref>{{cite web |url=http://www.brisbaneinternational.com.au/2013/01/dimitrov-downs-baghdatis-in-thriller|title=Dimitrov downs Baghdatis to reach first final|access-date=4 January 2013}}</ref> He lost to world No. 3 and defending champion [[Andy Murray]] in straight sets, despite being a break up in both sets.<ref>{{cite news|title=Andy Murray beats Dimitrov 7–6 (0), 6–4 to defend title at Brisbane International |url=https://www.foxnews.com/sports/andy-murray-beats-dimitrov-7-6-0-6-4-to-defend-title-at-brisbane-international/|access-date=6 January 2013 | work=Fox News|date=6 January 2013}}</ref> Dimitrov paired [[Kei Nishikori]] in the doubles and reached the semifinals, but withdrew due to Nishikori's injury. This performance also meant that Dimitrov surpassed $1 million earned in prize money,<ref name=1_million_earned>{{cite web|title=Гришо спечели над 1 млн. долара от наградни фондове|url=http://www.pik.bg/grisho-specheli-nad-1-mln-dolara-ot-nagradni-fondove/|access-date=7 January 2013|url-status=dead|archive-url=https://archive.today/20130407133320/http://www.pik.bg/grisho-specheli-nad-1-mln-dolara-ot-nagradni-fondove/|archive-date=7 April 2013|df=dmy-all}}</ref> a feat which no other male Bulgarian tennis player has accomplished. In his next event, the [[2013 Apia International Sydney|Sydney International]], Dimitrov suffered a first-round straight-set loss to Italian [[Fabio Fognini]].<ref>{{cite web|title=Sydney: Fognini stuns Dimitrov|url=http://www.ubitennis.com/english/sport/tennis/2013/01/08/827317-sydney_fognini_stuns_dimitrov.shtml|access-date=9 January 2013|archive-date=10 January 2013|archive-url=https://web.archive.org/web/20130110180218/http://www.ubitennis.com/english/sport/tennis/2013/01/08/827317-sydney_fognini_stuns_dimitrov.shtml|url-status=dead}}</ref>

At the [[2013 Australian Open – Men's singles|Australian Open]], Dimitrov suffered a first-round straight-set defeat by Julien Benneteau.<ref>{{cite news|title=Australian Open 2013 diary: Dimitrov dumped out, Sharapova storms through|url=https://www.theguardian.com/sport/blog/2013/jan/14/australian-open-diary-dimitrov-sharapova|access-date=14 January 2013 | location=London|work=The Guardian|first=Kevin|last=Mitchell|date=14 January 2013}}</ref> He also competed in the men's doubles event with Marcos Baghdatis. The pair defeated fourth seeds [[Max Mirnyi]] and [[Horia Tecău]] in the second round,<ref>{{cite web|title=Dimitrov, Baghdatis Make It to Australian Open 3rd Round|url=http://www.novinite.com/view_news.php?id=146986|access-date=19 January 2013}}</ref> before losing to [[Juan Sebastián Cabal]] and [[Robert Farah Maksoud]] in the third round in two close tie-break sets.<ref>{{cite web|title=Гришо и Багдатис отпаднаха на двойки в Австралия| date=21 January 2013 |url=http://corner.dir.bg/news.php?id=12872287|access-date=21 January 2013}}</ref> Despite losing in the first round, Dimitrov became the first male Bulgarian player to rank inside the top 40 after the event.<ref name=Top40_reached>{{cite web|title=Григор Димитров влезе в Топ 40|date=28 January 2013|url=http://www.webcafe.bg/id_1973274078|access-date=28 January 2013}}</ref> He then competed for Bulgaria in the [[Davis Cup]] against Finland, and won both his singles matches against [[Juho Paukku]] and Micke Kontinen, but lost his doubles in five sets (with partner [[Dimitar Kuzmanov]]) against [[Henri Kontinen]] of Finland and [[Harri Heliövaara]]. Finland ended up winning the tie 3–2.

At the [[2013 PBZ Zagreb Indoors – Singles|Zagreb Indoors]], Dimitrov lost in the first round to [[Ivo Karlović]] in two tie-breaks.<ref>{{cite news |url=http://www1.skysports.com/tennis/news/12110/8474387/Ivo-Karlovic-beats-Grigor-Dimitrov-in-two-tie-breaks-at-PBZ-Zagreb-Indoors|title=Ivo Karlovic beats Grigor Dimitrov in two tie-breaks at PBZ Zagreb Indoors|access-date=5 February 2013 | publisher=Sky Sports}}</ref> At the [[2013 ABN AMRO World Tennis Tournament – Singles|Rotterdam Open]], Dimitrov beat [[Bernard Tomic]] and Nikolai Davydenko, and Marcos Baghdatis in three sets.<ref>{{cite web |url=http://www.stevegtennis.com/2013/02/dimitrov-beats-tomic-in-first-round-of-rotterdam-janowicz-out/|title=Dimitrov beats Tomic in first round of Rotterdam, Janowicz out|date=11 February 2013 |access-date=11 February 2013}}</ref><ref>{{cite web|title=Grigor Dimitrov beats Nikolay Davydenko in Rotterdam|url=http://bg-daily-news.eu/sport/509-grigor-dimitrov-beats-nikolay-davydenko-in-rotterdam|access-date=14 February 2013|url-status=dead|archive-url=https://web.archive.org/web/20131202224920/http://bg-daily-news.eu/sport/509-grigor-dimitrov-beats-nikolay-davydenko-in-rotterdam|archive-date=2 December 2013|df=dmy-all}}</ref><ref>{{cite web|title=Dimitrov outlasts Baghdatis in ABN quarterfinals|website=[[Miami Herald]]|url=http://www.miamiherald.com/2013/02/14/3235042/federer-advances-to-quarterfinals.html|access-date=14 February 2013}}</ref> In the semifinals, Dimitrov lost against world No. 7 and eventual champion, [[Juan Martín del Potro]], in straight sets.<ref>{{cite web|title=Del Potro beats Dimitrov in ABN AMRO semifinals|url=http://www.utsandiego.com/news/2013/feb/16/del-potro-beats-dimitrov-in-abn-amro-semifinals/|access-date=16 February 2013}}</ref> At the [[2013 BNP Paribas Open|Indian Wells Open]], Dimitrov became the first Bulgarian male tennis player to be seeded in a [[ATP World Tour Masters 1000|Masters 1000]] event.<ref>{{cite web|title=Официално, Григор поставен в Индиън Уелс, близо е до мач с Джокович|url=http://zonasport.bg/article/tenis/ofitsialno-grigor-postaven-v-indian-uels-blizo-e-do-mach-s-dzhokovich.html|access-date=6 March 2013|archive-date=23 May 2013|archive-url=https://web.archive.org/web/20130523020028/http://zonasport.bg/article/tenis/ofitsialno-grigor-postaven-v-indian-uels-blizo-e-do-mach-s-dzhokovich.html|url-status=dead}}</ref> In singles, he beat [[Matthew Ebden]] in two sets, but lost to world No. 1 Novak Djokovic in the third round.<ref>{{cite web|title=Димитров загуби от №1 в света|date=13 March 2013|url=http://topsport.ibox.bg/news/id_1556382672|access-date=13 March 2013}}</ref> In doubles he partnered with [[Frederik Nielsen]]; they lost to Ivan Dodig and [[Marcelo Melo]] in the second round.<ref>{{cite web|title=Григор отпадна и на двойки в Индиън Уелс|url=http://www.bnews.bg/article-71724|access-date=13 March 2013}}</ref> At the [[2013 Sony Open Tennis – Men's singles|Miami Open]], Dimitrov beat [[Simone Bolelli]], but lost to second seed Andy Murray in straight sets in the following round.<ref>{{cite web|title=Murray advances at Miami Masters|url=http://www.sbs.com.au/news/article/1750424/Murray-advances-at-Miami-Masters|access-date=26 March 2013|archive-date=26 March 2013|archive-url=https://web.archive.org/web/20130326081331/http://www.sbs.com.au/news/article/1750424/Murray-advances-at-Miami-Masters|url-status=dead}}</ref> In [[2013 Sony Open Tennis – Men's doubles|doubles]] with partner [[Frederik Nielsen]], they reached semi-finals losing in straight sets against the eighth seeds, [[Mariusz Fyrstenberg]] and [[Marcin Matkowski]].<ref>{{cite web|title=Григор Димитров и Нилсен отпаднаха на полуфинал в Маями|date=30 March 2013|url=http://www.dnevnik.bg/sport/2013/03/30/2032518_grigor_dimitrov_i_nilsen_otpadnaha_na_polufinal_v/|access-date=30 March 2013}}</ref>

[[File:Grigor Dimitrov - Monte-Carlo 2013 - 001.jpg|right|thumb|upright=.7|Dimitrov at the 2013 Monte-Carlo Masters]]
Dimitrov's next tournament was the clay-court [[2013 Monte-Carlo Rolex Masters – Singles|Monte-Carlo Masters]], where he reached his first quarterfinal at this level beating [[Xavier Malisse]], eighth seed Janko Tipsarević, and [[Florian Mayer]], all in straight sets,<ref>{{cite web|url=https://sofiaglobe.com/2013/04/18/bulgarias-dimitrov-books-quarterfinal-date-with-nadal-at-monte-carlo-masters/|title= Bulgaria's Dimitrov books quarterfinal date with Nadal at Monte-Carlo Masters|date=18 April 2013}}</ref> but lost in three sets to eight-time defending champion and third seed Rafael Nadal.<ref>{{cite news|title=Rafael Nadal beats Grigor Dimitrov at Monte-Carlo Masters|url=http://sportsillustrated.cnn.com/tennis/news/20130419/monte-carlo-masters-rafael-nadal.ap/|archive-url=https://web.archive.org/web/20130918115443/http://sportsillustrated.cnn.com/tennis/news/20130419/monte-carlo-masters-rafael-nadal.ap/|url-status=dead|archive-date=18 September 2013|access-date=19 April 2013 | work=CNN|date=19 April 2013}}</ref> This good run in Monte Carlo meant Dimitrov entered the top 30 in the ATP rankings for the first time, at No. 28. His next event was [[2013 Barcelona Open Banco Sabadell – Singles|Barcelona Open]], seeded 14th, he received a bye, but lost in the second round, despite leading 5–2 in the first set, he lost in straight sets to in-form [[Tommy Robredo]].<ref>{{cite web|title=Гришо отпадна безславно от турнира в Барселона след 0:2 срещу Робредо|url=http://www.winner.bg/editors-choice/read79351.html|access-date=24 April 2013|url-status=dead|archive-url=https://web.archive.org/web/20130615125700/http://www.winner.bg/editors-choice/read79351.html|archive-date=15 June 2013|df=dmy-all}}</ref>

At the [[2013 Mutua Madrid Open – Men's singles|Madrid Open]], following a victory over fellow 21-year-old [[Javier Martí]], Dimitrov recorded the biggest win of his career, defeating world No. 1, Novak Djokovic in a three set match, in just over three hours. The two had met twice before, with Djokovic taking both encounters. In the third round, despite winning the first set, he lost in three sets to 15th seed Stan Wawrinka.<ref>{{cite web|title=Вавринка пречупи Григор и го изхвърли от Мадрид|url=http://www.bnews.bg/article-76054|access-date=10 May 2013}}</ref>

Dimitrov's next event was at the [[2013 Italian Open – Men's singles|Internazionali d'Italia]]. In what was his fourth victory over the Cypriot out of five matches, he beat Marcos Baghdatis in straight sets in the first round, with one break of serve deciding both sets. In the second round he lost in straight sets against ninth seed and world No. 9 Richard Gasquet – his fourth loss against the Frenchman out of four matches.<ref>{{cite web|title=DJOKOVIC BEGINS TITLE QUEST; GASQUET OUSTS DIMITROV FOR THIRD ROUND BERTH|url=http://www.atpworldtour.com/News/Tennis/2013/05/20/Rome-Tuesday-Djokovic-Berdych-Gasquet.aspx|access-date=14 May 2013}}</ref>

At the [[2013 French Open – Men's singles|French Open]], Dimitrov was seeded 26th, thus becoming the first ever Bulgarian male tennis player to be seeded at a Grand Slam tournament.<ref>{{cite web|title=Григор Димитров поставен под № 28 на "Ролан Гарос"|url=http://www.blitz.bg/sport/article/177991|access-date=20 May 2013}}</ref> He beat [[Alejandro Falla]] in the first round, after the Colombian retired trailing one set to love and one game down in the second set, citing an elbow problem.<ref>{{cite web|title=Григор победи Фая за 58 минути|url=http://pik.bg/%D0%B3%D1%80%D0%B8%D0%B3%D0%BE%D1%80-%D0%BF%D0%BE%D0%B1%D0%B5%D0%B4%D0%B8-%D1%84%D0%B0%D1%8F-%D0%B7%D0%B0-58-%D0%BC%D0%B8%D0%BD%D1%83%D1%82%D0%B8-news76229.html|access-date=28 May 2013}}</ref> Dimitrov eliminated wildcard world No. 324, [[Lucas Pouille]], in straight sets in the second round, thus becoming the first ever Bulgarian male tennis player to reach the third round of a Grand Slam.<ref>{{cite web|title=Григор с лекота стигна III кръг на Ролан Гарос|url=http://www.bnews.bg/article-77862|access-date=30 May 2013}}</ref> He lost in straight sets against world No. 1, Novak Djokovic, in the third round.<ref>{{cite web|title=Григор не успя да сътвори сензацията срещу Джокович в Париж|url=http://gong.bg/view_article.php?article_id=350187|access-date=1 June 2013}}</ref>
Dimitrov also played in the [[2013 French Open – Men's doubles|doubles]] with partner Frederik Nielsen losing in straight sets to seventh seeded [[Alexander Peya]] and [[Bruno Soares]] in the second round.

[[File:Dimitrov WM13-021 (9482641359).jpg|thumb|upright=.7|left|Dimitrov at Wimbledon, 2013]]
In the grass season, Dimitrov played the [[2013 Aegon Championships – Singles|Birmingham Championships]], where he was seeded tenth. He faced [[Dudi Sela]] in the first round, he came back from a set down and won the third set in a tie-break, but lost to four-time champion [[Lleyton Hewitt]] in the second round in straight sets. He then played the [[Boodles Challenge]], an exhibition event, he lost to Janko Tipsarević and Novak Djokovic on a match tie-break, but defeated [[Jerzy Janowicz]] in straight sets.<ref>{{cite web|title=Григор Димитров победи Янович на The Boodles|url=http://www.standartnews.com/sport-sport/grigor_dimitrov_pobedi_yanovich_na_the_boodles-193416.html|access-date=21 June 2013|archive-date=4 March 2016|archive-url=https://web.archive.org/web/20160304202532/http://www.standartnews.com/sport-sport/grigor_dimitrov_pobedi_yanovich_na_the_boodles-193416.html|url-status=dead}}</ref> At the [[2013 Wimbledon Championships|Wimbledon Championships]], Dimitrov eliminated Simone Bolelli in straight sets and then lost in the second round to world No. 55, [[Grega Žemlja]], 11–9 in the fifth set.<ref>{{cite news|title=Grigor Dimitrov exits Wimbledon 2013 with defeat to Grega Zemlja|url=https://www.theguardian.com/sport/2013/jun/28/gregor-dimitrov-wimbledon-2013-grega-zemlja|newspaper=guardian.co.uk | location=London|first=Simon|last=Cambers|date=28 June 2013}}</ref>

At [[2013 Swedish Open|Swedish Open]], Dimitrov reached semifinals for his second consecutive year. He eliminated
Elias Ymer and [[Filippo Volandri]] in three sets, and upset world No. 20, Juan Mónaco, in the quarterfinals, in straight sets.<ref>{{cite news|title=Dimitrov Cruises Past Monaco to Reach Bastad Semifinal|url=http://www.novinite.com/view_news.php?id=151970|newspaper=novinite.com}}</ref>  In the semifinals he lost to [[Fernando Verdasco]], in an epic three set battle.<ref>{{Cite web|url=https://www.tennisworldusa.org/tennis/news/ATP_Tennis/11386/fernando-verdasco-beats-grigor-dimitrov-to-reach-final-in-gastad/|title=Fernando Verdasco beats Grigor Dimitrov to reach final in Gastad|date=13 July 2013|website=Tennis World USA|accessdate=26 June 2023}}</ref> He then started his [[2013 US Open Series|US Open Series]] campaign at the [[2013 Citi Open|Washington Open]], Dimitrov received a bye and defeated [[Xavier Malisse]] and [[Sam Querrey]] in straight sets.<ref>{{cite news|title=Григор Димитров е на 1/4-финалите във Вашингтон|url=http://www.segabg.com/article.php?id=659676|date=2 August 2013|language=bg}}</ref><ref>{{cite news|title=Querrey gets a scare in Citi Open|url=http://msn.foxsports.com/tennis/story/citi-open-angelique-kerber-jack-sock-sam-querrey-advance-073013|work=Fox Sports|date=31 July 2013}}</ref> In the quarterfinals, Dimitrov lost in two tiebreak sets to the German veteran [[Tommy Haas]].<ref>{{cite news|title=Tommy Haas, Grigor Dimitrov|url=http://www.newsdaily.com/europe/a5982e107e08d14989685bd457530282/tommy-haas-grigor-dimitrov|access-date=3 August 2013|archive-date=3 December 2013|archive-url=https://web.archive.org/web/20131203002615/http://www.newsdaily.com/europe/a5982e107e08d14989685bd457530282/tommy-haas-grigor-dimitrov|url-status=dead}}</ref> At the [[2013 Rogers Cup|Rogers Cup]], he fell in the first round the Spaniard [[Marcel Granollers]] in straight sets, but rebounded at the [[2013 Western & Southern Open|Western & Southern Open]], defeating world No. 15 Nicolás Almagro and [[Brian Baker (tennis)|Brian Baker]], before losing to Rafael Nadal in three sets in the third round. The Bulgarian then suffered three consecutive first round exits at the [[2013 US Open (tennis)|US Open]] to [[João Sousa]] in five sets, the [[2013 China Open (tennis)|China Open]] to [[Roberto Bautista Agut]] in straight set, and the [[2013 Shanghai Rolex Masters|Shanghai Masters]] to [[Kei Nishikori]] in straight sets as well.

At the [[2013 If Stockholm Open|Stockholm Open]] Dimitrov won his first ATP title by defeating top seed David Ferrer in the final, coming back from a set down, becoming the first ever male Bulgarian player in the Open era to win such a title. This win also meant Dimitrov reached a career-best No. 22 in the world. He followed it up with a quarterfinal showing at the [[2013 Swiss Indoors|Swiss Indoors]] defeating [[Radek Štěpánek]] and Alexandr Dolgopolov in straight sets, before losing to childhood idol [[Roger Federer]] in two tight sets. He played his final event of the year at the [[2013 BNP Paribas Masters|Paris Masters]], where he beat [[Michaël Llodra]] and Fabio Fognini, both in three sets, but then lost to Juan Martín del Potro in the third round, despite winning the first set. Dimitrov finished the year ranked 23rd in singles and 68th in doubles.

On 16 December 2013, Dimitrov received the second most votes for the [[Bulgarian Sportsperson of the Year]] award, earning 1331 points and finishing just behind wrestler [[Ivo Angelov]].<ref>{{cite news|title=Борецът Иво Ангелов е "Спортист на 2013 година"!|url=http://topsport.ibox.bg/material/id_1650356565|publisher=topsport.bg|date=16 December 2013|access-date=16 December 2013}}</ref>

===2014: Three titles on three surfaces, Wimbledon semifinal, top 10===
Dimitrov started the 2014 season ranked 23rd. His first event was the [[2014 Brisbane International|Brisbane International]], where he took part in the last event too and reached his first final at that time. He was now seeded fifth. However, now he was unable to repeat that good performance, winning in the first round in two sets against [[Robin Haase]] in under one hour, but then losing against [[Marin Čilić]] in two sets,<ref>{{cite web|title=Чилич: С победата над Григор поставям ново начало
|url=http://www.sportal.bg/news.php?news=465051|access-date=1 January 2014}}</ref> losing both sets to five games with a break of his serve in the last game deciding both sets. He also competed in the doubles with partner [[Jérémy Chardy]] and won in the first round against Brits [[Colin Fleming|Fleming]] and [[Ross Hutchins|Hutchins]]<ref>{{cite web|title=Григор Димитров с победа и загуба навръх Нова година| date=January 2014 |url=http://shum.bg/index.php?item=102816|access-date=1 January 2014}}</ref>  (winning the deciding champion tiebreak), but then lost in the second round against Federer and Mahut<ref>{{cite web|title=Григор губи и на двойки в Бризбейн|url=http://narodensport.eu/?p=113308|access-date=2 January 2014|archive-date=19 April 2014|archive-url=https://web.archive.org/web/20140419182532/http://narodensport.eu/?p=113308|url-status=dead}}</ref> in a match which featured three tiebreaks, with a champion tiebreak again deciding the match. Dimitrov then played at the exhibition tournament in [[AAMI Classic|Kooyong]], Australia, an event which featured top players Richard Gasquet, Stan Wawrinka and Tomáš Berdych. However he failed to take a single victory (losing in straight sets to Kei Nishikori<ref>{{cite web|title=Гришо губи в Куйонг|date=9 January 2014 |url=http://www.duma.bg/node/69507|access-date=9 January 2014}}</ref> and [[Fernando Verdasco]]<ref>{{cite web|title=Слаб Гришо падна и от Вердаско|url=http://www.novinar.net/news/slab-grisho-padna-i-ot-verdasko_NDUyMTs2Ng==.html|archive-url=https://archive.today/20140419084446/http://www.novinar.net/news/slab-grisho-padna-i-ot-verdasko_NDUyMTs2Ng==.html|url-status=dead|archive-date=19 April 2014|access-date=9 January 2014}}</ref>), and ultimately pulled out prior to the seventh place playoff.

Seeded 22nd at the [[2014 Australian Open|Australian Open]], Dimitrov had his best run at a major event, defeating [[Bradley Klahn]],<ref>{{cite web|title=Победа за Григор Димитров на Australian Open|url=http://www.dnes.bg/drugi-sportove/2014/01/14/pobeda-za-grigor-dimitrov-na-australian-open.212357|access-date=14 January 2014}}</ref> [[Lu Yen-hsun]],<ref>{{cite web|title=Победа в три сета и Григор е в третия кръг на Australian Open (ВИДЕО + ГАЛЕРИЯ)|url=http://www.sportal.bg/news.php?news=467408|access-date=16 January 2014}}</ref> eleventh seed Milos Raonic and Roberto Bautista Agut in succession, leading him to his first ever major quarterfinal, where he lost to top seed and [[List of ATP number 1 ranked singles players|world No. 1]] Rafael Nadal in four sets,<ref>{{cite web|title=Надал прекрати участието на Григор Димитров в Мелбърн|date=22 January 2014 |url=http://www.mediapool.bg/nadal-prekrati-uchastieto-na-grigor-dimitrov-v-melbarn-news215868.html|access-date=22 January 2014}}</ref> after winning the first and also having three set points to win the third. As a result of this career-best run at a Grand Slam tournament, Dimitrov entered the world's top 20 for the first time (at No. 19),<ref name="top 20">{{cite web|title=Григор Димитров влезе в топ 20 на световната ранглиста|date=27 January 2014 |url=http://www.mediapool.bg/grigor-dimitrov-vleze-v-top-20-na-svetovnata-ranglista-news216037.html|access-date=27 January 2014}}</ref> becoming the first ever Bulgarian male tennis player to do so.

Next, in February, he played at the [[2014 ABN AMRO World Tennis Tournament – Singles|Rotterdam]] indoor event, where he was seeded eighth. Dimitrov beat world No. 28 Dmitry Tursunov in the first round 2–1 sets. Dimitrov then lost to world No. 24, Ernests Gulbis, in straight sets.<ref>{{cite web|title=Григор отстъпи пред Гулбис в Ротердам|url=http://www.sportal.bg/news.php?news=472242&com_page=3|access-date=13 February 2014}}</ref>

[[File:Григор Димитров с купата си от.jpg|thumb|upright=.7|left|Dimitrov with the trophy at the [[2014 Abierto Mexicano Telcel|Acapulco]] event]]
Dimitrov played in the [[2014 Abierto Mexicano Telcel|Acapulco]] hard court event, where he was seeded 4th. Dimitrov beat world No. 71, [[Marinko Matosevic]], in the first round and Marcos Baghdatis in the second in straight sets. In the quarterfinals, Dimitrov beat seventh seed and world No. 18, Ernests Gulbis, in two sets to one in a match lasting over 2½ hours. In the semifinals Dimitrov beat second seed and world No. 7, Andy Murray, for the first time in a match that lasted almost three hours – losing the first set then overcoming the Brit in two tiebreaks; thus, reaching his third ATP final where he defeated Kevin Anderson, in three sets. The victory was Dimitrov's first win at an ATP 500 level tournament<ref>{{cite web|url=https://www.bbc.co.uk/sport/tennis/26404791|title=Mexican Open: Grigor Dimitrov beats Kevin Anderson in final|date=2 March 2014|publisher=BBC Sport}}</ref> and with it he reached his highest ever ATP rank – No. 16. Following his win, Dimitrov played at the [[2014 BNP Paribas Open|Indian Wells Masters]], an ATP 1000 event, where he was seeded 15th and received a bye into the second round where he beat Robin Haase in straight sets, but then lost in the third round in two sets to one to world No. 22, Ernests Gulbis, who reached the quarterfinal.

Dimitrov then played in [[2014 Sony Open Tennis – Men's singles|Miami]], where he was again seeded 15th and had a bye in the first round. He beat [[Albert Montañés]] 2–1 sets (losing the second set on a tiebreak) in round two. In the third round, in what was his second loss against the Japanese out of two matches between them, he lost in a tight two sets to 20th seed Kei Nishikori, who went on to reach the semifinals. After Miami, Dimitrov reached a new career-high ranking of No. 15.

In April, he played for the Bulgarian [[Davis Cup]] team in the Europe Group II playoffs between Greece and Bulgaria. In the opening match of the tie, he beat No. 690 teenager Markos Kalovelonis 3–0 sets, losing just six games. He then teamed up with No. 344 [[Dimitar Kutrovsky]], who previously brought a second win for Bulgaria, and they beat the Greek team of [[Alexandros Jakupovic]] and Markos Kalovelonis 3–0 sets, thus bringing the tie to a crucial 3–0 lead, meaning Bulgaria keeps their Europe Group II position for 2015 and Greece gets relegated to Europe Group III.

Just before [[2014 Monte-Carlo Rolex Masters – Singles|Monte Carlo]], Dimitrov reached a new career-high ranking of No. 14.<ref>{{cite web|title=Григор Димитров е вече 14-ти в света, Цвети Пиронкова е в топ 40 |date=14 April 2014 |url=http://tennis.actualno.com/Grigor-Dimitrov-e-veche-14-ti-v-sveta-Cveti-Pironkova-e-v-top-40-news_23796.html|access-date=14 April 2014}}</ref> At the [[2014 Monte-Carlo Rolex Masters – Singles|Monte-Carlo Masters]] clay-court event, he was seeded 12th. Dimitrov beat in-form No. 32 [[Marcel Granollers]] 2–1 sets in the 1st round, then another Spaniard – qualifier [[Albert Ramos]], ranked just outside the top-100, also 2–1 sets. However, in what was his fourth loss out of five matches between them, Dimitrov lost 2–0 sets to sixth seed David Ferrer in round three.

He then played in the [[2014 BRD Năstase Țiriac Trophy – Singles|Bucharest]] clay-court event, where he was given a wildcard and was the top seed and had a bye in the first round. In what was the first meeting between the two, in round two Dimitrov beat No. 79 [[Jiří Veselý]] 2–0 sets. He beat [[Sergiy Stakhovsky]] 2–0 sets in round three, then beat third seed No. 24 Gaël Monfils in the semifinals after leading in the first set when Monfils retired,<ref>{{cite web|title=Григор Димитров стигна финала в Букурещ след отказване на Монфис|date = 26 April 2014|url=http://www.dnevnik.bg/sport/2014/04/26/2288501_grigor_dimitrov_stigna_finala_v_bukuresht_sled/?ref=rss|access-date=26 April 2014}}</ref>  thus reaching his fourth ATP final. In the final, Dimitrov defeated [[Lukáš Rosol]] 2–0 sets, winning the first on a tie-break, then winning the second set with the loss of just one game to win his third ATP title and first one on clay.<ref>{{cite web|title=Григор Димитров триумфира в Букурещ с трета титла в кариерата си|date=27 April 2014|url=http://www.dnevnik.bg/sport/2014/04/27/2288887_grigor_dimitrov_triumfira_v_bukuresht_s_treta_titla_v/|access-date=27 April 2014}}</ref>

In May, he played in the [[2014 Mutua Madrid Open – Men's singles|Madrid Open]] clay-court event, where he was seeded 12th. Dimitrov beat local wildcard [[Pablo Carreño Busta]] 2–0 sets in the first round,<ref>{{cite web|title=Григор Димитров започна със стил в Мадрид|date=6 May 2014 |url=http://tennis.actualno.com/Grigor-Dimitrov-zapochna-sys-stil-v-Madrid-news_26802.html|access-date=6 May 2014}}</ref> then in the second round another wildcard – No. 164 [[Marius Copil]] – 2–1 sets, coming back from a set down, winning the deciding set on a tie-break. However, in what was his first loss against the Czech out of three matches between them, in round three he lost 2–1 sets to sixth seed No. 6, Tomáš Berdych, after winning the first set.

Dimitrov then played at the [[2014 Italian Open – Men's singles|Italian Open]], where he was again seeded 12th. He beat No. 47 [[Édouard Roger-Vasselin]] 2–1 sets, No. 52 Ivo Karlović 2–0 sets, then sixth seed, Tomáš Berdych, 2–1 for a third victory against the Czech out of four matches between them, then 15th seed Tommy Haas in the quarterfinals, after the German retired while losing 1–0 in sets. In what was the fifth match between them and the first match that Dimitrov was unable to win a set in, he lost 2–0 sets to first seed, Rafael Nadal, in the semifinals. This reaching of the Rome semifinal was Dimitrov's best ATP Masters performance. He also successfully played in [[2014 Italian Open – Men's doubles|the Rome doubles]] with partner Lukáš Rosol and they beat unseeded world No. 4 Colombian pair [[Juan Sebastián Cabal]] and [[Robert Farah Maksoud]] in the first round 2–0 sets, winning both sets on a tie-break. In the second and third rounds, they beat second seeded Austrian-Brazilian duo of [[Alexander Peya]] and [[Bruno Soares]] then unseeded Marin Čilić and [[Santiago González (tennis)|Santiago González]], both 2–1 sets. They lost 2–0 sets to undeeded Robin Haase and Feliciano López in the semifinals. This performance meant Dimitrov reached a new career-best singles ranking of 12th,<ref name=May_2014_best_rank>{{cite web|title=Григор Димитров с ново рекордно класиране – вече е №12 в света|url=http://offnews.bg/news/%D0%A1%D0%BF%D0%BE%D1%80%D1%82_18752/%D0%93%D1%80%D0%B8%D0%B3%D0%BE%D1%80-%D0%94%D0%B8%D0%BC%D0%B8%D1%82%D1%80%D0%BE%D0%B2-%D1%81-%D0%BD%D0%BE%D0%B2%D0%BE-%D1%80%D0%B5%D0%BA%D0%BE%D1%80%D0%B4%D0%BD%D0%BE-%D0%BA%D0%BB%D0%B0%D1%81%D0%B8%D1%80%D0%B0%D0%BD%D0%B5-%D0%B2%D0%B5%D1%87%D0%B5-%D0%B5-12-%D0%B2-%D1%81%D0%B2%D0%B5%D1%82%D0%B0_336900.html|access-date=19 May 2014}}</ref> and also moved 58 places up the doubles rankings, to No. 84.<ref name="May_2014_best_rank"/>

He then played at [[2014 French Open – Men's singles|French Open]], where he was seeded 11th. In round one he lost 3–0 sets to big-serving No. 37 Ivo Karlović, whom he recently beat in Rome.

In June, Dimitrov played at the [[2014 Aegon Championships – Singles|Queens]] grass-court event, where he was seeded fourth and had a bye into round two. He beat local No. 168 [[James Ward (tennis)|James Ward]] in round two, then No. 53 Édouard Roger-Vasselin in the third round, both 2–0 sets. Dimitrov was due to play eighth seed Alexandr Dolgopolov in the quarterfinals, but received a walkover when the Ukrainian retired before the match, citing a thigh injury. Dimitrov then faced first seed, Stan Wawrinka, in the semifinals, and won in straight sets. Dimitrov claimed his first title on a grass court against Feliciano López in three sets, being a set behind and saving a match point. It was the event's first time in which the final was decided with three tiebreakers, as well as being the longest ever Queen's final. Dimitrov also played in [[2014 Aegon Championships – Doubles|the Queens doubles event]], with partner world No. 3 Wawrinka (ranked outside the top 150 in the ATP doubles rankings), and in round one they beat local brother wildcard duo of [[Ken Skupski|Ken]] and [[Neal Skupski]] in straight sets, but then lost in a tight two-setter to third-seeded Canadian-Serbian veteran duo of [[Daniel Nestor]] and [[Nenad Zimonjić]] in the second round.

Next, Dimitrov played at the [[2014 Wimbledon Championships – Men's singles|2014 Wimbledon Championships]], where he was seeded 11th. In rounds one and two he beat two qualifiers —No. 150 [[Ryan Harrison]] and No. 236 [[Luke Saville]], both in three sets. In round three, in what was his second victory against the Ukrainian out of three matches, he beat 21st seed [[Alexandr Dolgopolov]] in a five-set match, coming back from 2–1 sets down. Dimitrov followed that up with a straight sets victory over No. 64 [[Leonardo Mayer]] in round four. In the quarterfinals, in what was his second victory against the Brit out of five matches, he beat defending Wimbledon champion and third seed Andy Murray 3–0 sets. This win meant Dimitrov reached his first Grand Slam semifinal, becoming the first male Bulgarian player to reach that stage. He was beaten in four sets by first seed No. 2, Novak Djokovic, who went on to win the tournament. This good performance also meant Dimitrov entered the top-10 ATP rankings for the first time – at No. 9 – becoming the first ever Bulgarian male tennis player to do so.<ref>{{cite web|title=ATP отбеляза влизането на Григор Димитров в топ 10|url=http://offnews.bg/video/ATP-%D0%BE%D1%82%D0%B1%D0%B5%D0%BB%D1%8F%D0%B7%D0%B0-%D0%B2%D0%BB%D0%B8%D0%B7%D0%B0%D0%BD%D0%B5%D1%82%D0%BE-%D0%BD%D0%B0-%D0%93%D1%80%D0%B8%D0%B3%D0%BE%D1%80-%D0%94%D0%B8%D0%BC%D0%B8%D1%82%D1%80%D0%BE%D0%B2-%D0%B2-%D1%82%D0%BE%D0%BF-10_15135.html|website=OFFNews|access-date=9 July 2014}}</ref>

In the end of July, Dimitrov was due to play at the [[2014 Citi Open|Washington Open]] hardcourt event, where he was seeded third, but had to withdraw due to flu and sinus problems. In August, he played at the [[2014 Rogers Cup – Men's singles|Canadian Open]] Masters, where he was seeded No. 7 and had a bye into the second round. In the second and third rounds Dimitrov beat [[Donald Young (tennis)|Donald Young]] and 17th seed Tommy Robredo, both 2–1 sets. Then, in the quarterfinals, in what was his fifth victory against the South-African out of six matches between them, he beat No. 21, Kevin Anderson, 2–1 sets, coming back from a set down and winning the deciding set on a tiebreak. In the semifinals, he lost to 13th seed and eventual champion, Jo-Wilfried Tsonga.

Next, Dimitrov played at the [[2014 Western & Southern Open – Men's singles|Cincinnati Masters]]. He was seeded seventh again and had a bye into the second round where he lost to [[Jerzy Janowicz]]. At the [[2014 US Open – Men's singles|US Open]], Dimitrov was seeded seventh. After Dimitrov defeated [[Ryan Harrison]] in the first round, Dudi Sela in the second, and David Goffin in the third, he lost to 20th seed Gaël Monfils in the round of 16 in three close sets, which dropped his tennis ranking to No. 10 after the tournament.

Along with Novak Djokovic and Rafael Nadal, Dimitrov competed in the annual September China Open tournament in Beijing. After defeating [[Fernando Verdasco]] and [[Pablo Andújar]], Dimitrov lost to world No. 1 Djokovic in the quarterfinals. Dimitrov's next tournament was the [[2014 Shanghai Rolex Masters – Singles|Shanghai Masters]], where he was seeded 10th. After defeating [[Denis Istomin]] in the first round, Dimitrov lost to the unseeded Julien Benneteau in the second round.

Dimitrov began the defense of his ATP maiden title in [[2014 Stockholm Open – Singles|Stockholm]], winning his second- and third-round matches with [[Teymuraz Gabashvili]] and [[Jack Sock]].<ref>{{cite news|title=Dimitrov Begins Title Defence In Stockholm|url=http://www.atpworldtour.com/News/Tennis/2014/10/42/Stockholm-Wednesday-Dimitrov-Anderson-Sock.aspx|publisher=atpworldtour.com|date=15 October 2014}}</ref> He beat [[Bernard Tomic]] in the semifinals, reaching his sixth career ATP World Tour singles final. Dimitrov lost the final to [[Tomáš Berdych]] in three sets.<ref>{{cite news|title=Berdych Denies Dimitrov Title Defence In Stockholm|url=http://www.atpworldtour.com/News/Tennis/2014/10/42/Stockholm-Final-Berdych-Dimitrov.aspx|publisher=atpworldtour.com|date=19 October 2014}}</ref>

In [[2014 Swiss Indoors – Singles|Basel]], Dimitrov beat teenager [[Alexander Zverev]] and [[Vasek Pospisil]] in first and second rounds, before losing to top-seeded and eventual champion, Roger Federer, at the quarterfinals for a second year in a row. At the [[2014 BNP Paribas Masters – Singles|Paris Masters]], Dimitrov beat [[Pablo Cuevas]] in the second round, but then lost to Andy Murray in the third. This was his last tournament for the year. Dimitrov had an opportunity to qualify for the [[2014 ATP World Tour Finals]], but he finished 11th. On 22 December 2014, Dimitrov was chosen as the [[Bulgarian Sportsperson of the Year]] (earning 1190 points), becoming the first tennis player to win the award.<ref name="topsport100005">{{cite news|url=http://topsport.ibox.bg/material/id_275200468|title=Григор Димитров е Спортист на годината 2014! Кобрата не успя да пребори Гришо|publisher=topsport.bg|date=22 December 2014 |language=bg|access-date=23 December 2014}}</ref>

===2015: Australian Open fourth round===
Dimitrov started the year ranked No. 11. In the beginning of January, he began his season at the [[2015 Brisbane International|Brisbane]] outdoor hard-court event, where he was seeded fourth and received a bye into the second round. There Dimitrov beat [[Jérémy Chardy]], coming back from a set down and winning the deciding set on a tiebreak. In the quarterfinals, he beat [[Martin Kližan]] in straight sets, but then lost to world No. 2 and eventual champion Roger Federer at the semifinals in less than an hour. Dimitrov also played in the [[2015 Brisbane International – Men's doubles|doubles]] event, paired with the Australian teenager [[Thanasi Kokkinakis]], with whom he reached the semifinals.

At the [[2015 Australian Open|Australian Open]], Dimitrov was seeded tenth. In the first round he overcame Dustin Brown in just 69 minutes, then in the second round he beat [[Lukáš Lacko]] in four sets and Marcos Baghdatis in five sets in the third round. Dimitrov lost to sixth seed and eventual runner-up, Andy Murray, in the fourth round in four sets. In February, Dimitrov participated in the [[2015 ABN AMRO World Tennis Tournament – Singles|Rotterdam Open]] indoor hard-court event, where he was seeded fifth. In the first round he beat the qualifier [[Paul-Henri Mathieu]] 2–1 sets, saving two match points in the second set, but then lost in straight sets to world No. 37, Gilles Müller, in the second round. Dimitrov played in [[2015 Abierto Mexicano Telcel – Men's singles|Acapulco]] next, where he was the defending champion and seeded third. He lost in the second round to [[Ryan Harrison]]. On 10 March 2015, Dimitrov played at an annual exhibition tournament in [[Madison Square Garden]] against Federer, defeating the Swiss star for the first time.<ref>{{cite news |title=Dimitrov Beats Federer in Exhibition at MSG |publisher=abc News |date=10 March 2015 |url=http://abcnews.go.com/Sports/wireStory/dimitrov-beats-federer-exhibition-msg-29544811 |access-date=10 March 2015}}</ref>

In March Dimitrov played at the [[2015 BNP Paribas Open – Men's singles|Indian Wells Masters]], where he was seeded 11th and had a bye into the second round, where he beat in three sets the Australian teenager and world No. 37, [[Nick Kyrgios]]. Dimitrov lost to world No. 19, Tommy Robredo, in the third round. Dimitrov also played at the doubles event, paired with [[Mardy Fish]], but they lost in the first round to Spaniards David Ferrer and Fernando Verdasco. Dimitrov was seeded ninth at the [[2015 Miami Open – Men's singles|Miami Masters]] and had a bye into the second round, where he beat [[Vasek Pospisil]], but then lost to the 22nd seed [[John Isner]] in the third round. Dimitrov began his clay season at the [[2015 Monte-Carlo Rolex Masters – Singles|Monte-Carlo Masters]]. He was seeded ninth and beat Verdasco in the first round, and then defeated in straight sets Fabio Fognini in the second round. In the third round, Dimitrov crushed in less than an hour the seventh seed and defending champion Stan Wawrinka and then lost in straight sets to Gaël Monfils in the quarterfinals. Dimitrov also played in the doubles, paired with [[Max Mirnyi]]. They reached the second round, where they lost to [[the Bryan brothers]].

Dimitrov decided not to defend his title in Bucharest, and instead he participated in the first edition of the [[2015 Istanbul Open|Istanbul]] event. He was seeded second and had a bye into the second round, where he defeated [[Andrey Golubev]]. In the quarterfinals Dimitrov beat Ivan Dodig, but then lost to [[Pablo Cuevas]] in the semifinals. Next, Dimitrov played at the [[2015 Mutua Madrid Open – Men's singles|Madrid Masters]], where he was seeded tenth. His opponent in the first round [[Donald Young (tennis)|Donald Young]] retired, after Dimitrov was leading by a set and by 3–0 games in the second set. Then, Dimitrov beat Fabio Fognini, coming back from a set down, and overcame eighth seed Stan Wawrinka in three sets in the third round. At the quarterfinals, Dimitrov lost in straight sets to third seed and two-time defending champion Rafael Nadal, which was his sixth defeat out of six matches between them. Dimitrov also played in the [[2015 Mutua Madrid Open – Men's doubles|doubles]] and reached the second round.

Dimitrov was unable to defend his semifinal at the [[2015 Italian Open – Men's singles|Rome Masters]] in May. He was seeded 10th and beat in straight sets [[Jerzy Janowicz]] in the first round, but then lost in three sets to Fabio Fognini, in what was the third match between them within a month. Next, Dimitrov lost in straight sets to Jack Sock at the [[2015 French Open – Men's singles|French Open]] in the first round despite being seeded tenth. Dimitrov exited the tournament early for a second year in a row.

In June, Dimitrov failed to defend his title at the [[2015 Aegon Championships – Singles|Queen's Club]] grass-court event, losing in the second round to Gilles Müller. Next, being seeded 11th, he played at the [[2015 Wimbledon Championships – Men's singles|Wimbledon Championships]] and in the first two-round eliminated [[Federico Delbonis]] and [[Steve Johnson (tennis)|Steve Johnson]]. Dimitrov lost in straight sets to Richard Gasquet in the third round, in what was his fifth defeat out of five matches against the Frenchman. Following that defeat, Dimitrov decided to part ways with coach [[Roger Rasheed]].<ref>{{cite web|url=https://www.theguardian.com/sport/2015/jul/07/grigor-dimitrov-wimbledon-roger-rasheed |title=Grigor Dimitrov parts with coach Roger Rasheed after run of bad form &#124; Wimbledon 2015 |work=The Guardian |date= 6 July 2015|accessdate=2021-11-23}}</ref>

In July, he participated in the [[2015 Davis Cup]] against Luxembourg, winning all his matches. In August, he started his US Open Series campaign in [[2015 Citi Open – Men's singles|Washington]], reaching the third round. Then, he played at the [[2015 Rogers Cup – Men's singles|Rogers Cup]], losing to Jack Sock in the second round. At the [[2015 Western & Southern Open – Men's singles|Cincinnati Masters]], Dimitrov was eliminated in the third round by the world No. 2, Andy Murray, having missed a match point in the third set. Dimitrov's weak performance continued at the [[2015 US Open – Men's singles|US Open]], where he lost in five sets to [[Mikhail Kukushkin]] in the second round.

In September, he hired [[Franco Davín]] as his coach.<ref>{{Cite web|url=https://www.tennis.com/news/articles/dimitrov-hires-del-potro-s-former-coach-franco-davin|title=Dimitrov hires Del Potro's former coach, Franco Davin|website=Tennis.com|accessdate=26 June 2023}}</ref> Dimitrov reached the quarterfinals in [[2015 Malaysian Open, Kuala Lumpur – Singles|Kuala Lumpur]] and then in the beginning of October had another first round exit in [[2015 Rakuten Japan Open Tennis Championships – Singles|Tokyo]]. After these tournament Dimitrov dropped out of top 20. After an unsuccessful Asia swing, Dimitrov traveled to Sweden to participate in the [[Stockholm Open]] and reached the quarterfinals where he was defeated by Tomáš Berdych in straight sets. Following that tournament, he traveled to Basel for the [[Swiss Indoors]] where he lost to Rafael Nadal in three sets in the round of 16. His last tournament for the year was [[Paris Masters|Paris]], where Dimitrov managed to eliminate Marin Čilić, before losing to Ferrer. He did not qualify for the [[ATP World Tour Finals]].

===2016: Second US Open fourth round===
Ranked world No. 28, Dimitrov began the season in [[2016 Brisbane International|Brisbane]], where he reached the quarterfinals, losing to Federer. Paired with Kei Nishikori, Dimitrov also reached the semifinals in the doubles, but withdrew due to shoulder soreness. The Bulgarian reached his seventh career final in [[2016 Apia International Sydney|Sydney]], losing to the defending champion [[Viktor Troicki]] in three sets and a tie-break in the third set. Next, Dimitrov recorded another defeat to Federer, his fifth overall between the two, in the third round of the [[2016 Australian Open – Men's singles|Australian Open]].

In February, Dimitrov decided to skip the first edition of [[ATP Sofia Open|Sofia Open]] in his homeland and participated in the [[2016 Delray Beach International Tennis Championships|Delray Beach]] event, where he lost to the unseeded [[Rajeev Ram]] in the semifinals. Next, Dimitrov lost to the in-form and eventual champion [[Dominic Thiem]] at the quarterfinals in [[2016 Abierto Mexicano Telcel – Men's singles|Acapulco]].

In March, seeded 23rd, Dimitrov had a bye into the second round of [[2016 BNP Paribas Open – Men's singles|Indian Wells]], but was upset by the German teenager Alexander Zverev. Dimitrov also had a bye into the second round of the [[2016 Miami Open – Men's singles|Miami Open]]. In the third round, he overcame the world No. 2, Andy Murray, coming back from a set down, but then lost to Gaël Monfils.

In April, Dimitrov began his clay-court season. He reached the second round of the [[2016 Monte-Carlo Rolex Masters – Singles|Monte-Carlo Masters]], losing to the 15th seed Gilles Simon in straight sets. Seeded 2nd, Dimitrov reached his eighth career final in the [[2016 Istanbul Open|Istanbul]] event, beating third seed, Ivo Karlović at the semifinals in two tie-breaks. In the final, against the unseeded [[Diego Schwartzman]], Dimitrov was serving for the match in the second set, but started cramping and then had a complete meltdown. After smashing two rackets, and being warned and penalized, Dimitrov smashed a third racket in the third set, which resulted in a match-ending penalty.<ref>{{cite news | url=http://www.abc.net.au/news/2016-05-02/grigor-dimitrov-smashes-three-racquets-to-concede-istanbul-open/7374924 | title=ABC NEWS: Grigor Dimitrov smashes three racquets | newspaper=ABC News | date=May 2016 | access-date=2 May 2016}}</ref><ref>{{cite web | url=https://www.espn.com/tennis/story/_/id/15442092/diego-schwartzman-wins-istanbul-open-grigor-dimitrov-melts-down | title=ESPN: Diego Schwartzman wins in Istanbul as Grigor Dimitrov melts down | date=May 2016 | access-date=2 May 2016}}</ref>

At the [[2016 Mutua Madrid Open – Men's singles|Madrid Masters]], Dimitrov was unable to defend his quarterfinal from the previous year, suffering a first round exit in straight sets to [[Pablo Carreño]], not having lost even a set to the Spaniard prior to that match. In the following week, Dimitrov's position in the ATP ranking deteriorated further to No.35, a three-year low. The Bulgarian was then beaten again by Alexander Zverev in first round of the [[2016 Italian Open – Men's singles|Rome]] Masters. This was followed by another first round loss at the [[2016 French Open – Men's singles|French Open]] to Viktor Troicki, this time in five sets.

In June, Dimitrov's downfall continued, as he played on grass courts in [[2016 MercedesCup|Stuttgart]] and in [[2016 Aegon Championships – Singles|London]], losing once again in the first rounds to the wildcard [[Juan Martín del Potro]] in straight sets, and to the returning from injury [[Janko Tipsarević]], respectively. Being unseeded at a Major for the first time since [[2013 Australian Open – Men's singles|2013]], Dimitrov ended his losing streak at the [[2016 Wimbledon Championships – Men's singles|2016 Wimbledon]], first beating qualifier [[Bjorn Fratangelo]] and then 16th seed Gilles Simon, before losing to [[Steve Johnson (tennis)|Steve Johnson]]. Soon after that, Dimitrov revealed that prior to Wimbledon he had split with his coach Franco Davín.<ref>{{cite news|title=Grigor Dimitrov reveals coaching split with coach Franco Davín before Wimbledon|url=http://sport360.com/article/tennis/wimbledon/184452/grigor-dimitrov-reveals-coaching-split-with-coach-franco-davin-before-wimbledon/|publisher=sport360.com|date=2 July 2016}}</ref> The Bulgarian hired [[Daniel Vallverdu]] as coach.<ref>{{cite web|title=El Desafío De Dimitrov Y Vallverdu|url=http://www.atpworldtour.com/es/news/dimitrov-vallverdu-cincinnati-2016-feature-parte-1|website=atpworldtour.com|access-date=18 August 2016|language=es}}</ref>

In July, Dimitrov was seeded 12th in [[2016 Citi Open|Washington Open]] and had a bye into the second round, but had another disappointment, as he lost in straight sets to No. 82, [[Dan Evans (tennis)|Daniel Evans]]. At [[2016 Rogers Cup – Men's singles|Rogers Cup]], Dimitrov survived another early elimination against [[Yūichi Sugita]] in the first round, coming back from a set down and facing 2–5 in the second set tiebreak. That was followed by an easy win against wildcard [[Denis Shapovalov]] and then Dimitrov beat Ivo Karlović in straight sets in the third round. The Bulgarian lost in three sets to third seed Nishikori in the quarterfinals. Paired with Wawrinka, he beat Lucas Pouille and Dominic Thiem in the [[2016 Rogers Cup – Men's doubles|doubles]], before losing to [[Henri Kontinen]] and [[John Peers]].

Dimitrov participated in the [[Tennis at the 2016 Summer Olympics – Men's singles|2016 Summer Olympics]] in the first half of August, but lost in the first round to ninth seed Marin Čilić. The Bulgarian then had a good run in [[2016 Western & Southern Open – Men's singles|Cincinnati]], reaching his third career Masters semifinal. He subsequently beat in straight sets [[Gilles Simon]] in the first round and then came back from a set to down to eliminate 16th seed, Feliciano López. In the third round Dimitrov won against second seed Wawrinka and then beat Steve Johnson in the quarterfinals, both in straight sets. In the semifinal he was stopped again by the eventual champion Marin Čilić, after allowing re-breaks twice in the third set. With his performance, the Bulgarian secured the second spot in the [[2016 US Open Series]] standings. In the following week, Dimitrov returned in top 30 of ATP ranking, jumping ten positions to No. 24 spot.

Seeded 22nd, Dimitrov played in the [[2016 US Open – Men's singles|2016 US Open]] and reached the fourth round for a second time in his career after beating en route [[Íñigo Cervantes]], Jérémy Chardy and [[João Sousa]] before losing in straight sets to second seed, Andy Murray, who allowed Dimitrov only five games in total.

Dimitrov moved to Asia to play in the inaugural [[2016 Chengdu Open – Singles|Chengdu Open]]. He was seeded third and reached the semifinals, where he lost to fifth seed [[Albert Ramos Viñolas]]. The Bulgarian then went to the final of the [[2016 China Open – Men's singles|Beijing]] event, beating Steve Johnson, sixth seed Lucas Pouille and gaining first victory over Rafael Nadal, who was ranked No. 4 at the moment. At the semifinals, the third seed, [[Milos Raonic]], withdrew prior to the match with Dimitrov due to ankle injury. Dimitrov lost the final to No. 2, Andy Murray, in two tight sets. The Bulgarian then participated in the [[2016 Shanghai Rolex Masters – Singles|Shanghai Masters]], where in the first round he overcame in straight sets 14th seed, Richard Gasquet, to whom Dimitrov had had a negative record of 0–5 losses, but in the second lost to qualifier [[Vasek Pospisil]], who had never beaten Dimitrov.

The Bulgarian returned to Europe and reached the semifinals in [[2016 Stockholm Open – Singles|Stockholm]], where he was stopped by the eventual champion Juan Martín del Potro. Dimitrov then played in [[2016 Swiss Indoors – Singles|Basel]], but exited the event with a first round loss against Gilles Müller. In his last tournament for the season, the [[2016 BNP Paribas Masters – Singles|Paris Masters]], Dimitrov lost in three sets to No. 1, Novak Djokovic, in the third round.

===2017: Major semifinal, Masters & ATP Finals titles, world No. 3===
Ranked world No. 17, Dimitrov had a flying start to the season in [[2017 Brisbane International|Brisbane]], reaching the final by defeating world No. 8, Dominic Thiem in the quarterfinals and then No. 3 and defending champion Milos Raonic in the semifinals. In the final he overcame world No. 5, Kei Nishikori, in three sets, winning his first ATP title in nearly three years, his last having been at Queen's Club in 2014. Dimitrov next moved on to play in the [[2017 Australian Open – Men's singles|2017 Australian Open]], where he extended his winning streak further, reaching the semifinals. Dimitrov beat 18th seed, Richard Gasquet, in the third round and 11th seed David Goffin in the quarterfinals, before being eliminated by Rafael Nadal in a five-set thriller, which lasted almost five hours, with Dimitrov failing to convert double break points in the fifth set when the score was 4–3 for Dimitrov.<ref>{{cite web|title=Nadal Edges Dimitrov In A Thriller|url=http://www.atpworldtour.com/en/news/nadal-dimitrov-australian-open-2017-friday-semifinals|publisher=ATP|access-date=27 January 2017}}</ref> The match with Nadal was later cited among the top 3 of best Grand Slam matches in 2017.<ref>{{cite web|title=Best Grand Slam Matches Of 2017: 5 To 3|url=http://www.atpworldtour.com/en/news/best-grand-slam-matches-2017-5-to-3|website=www.atpworldtour.com|access-date=7 December 2017}}</ref><ref>{{cite web|title=NO. 2 OF '17: FOR NADAL, IT WAS DÉJA VÙ DOWN UNDER AGAINST DIMITROV|url=http://www.tennis.com/pro-game/2017/12/no-2-top-10-matches-australian-open-atp-tour-tennis-rafael-nadal-grigor-dimitrov/70789/|website=tennis.com|access-date=24 December 2017}}</ref>

In February, Dimitrov competed in the [[2017 Garanti Koza Sofia Open – Singles|Sofia Open]], where he was seeded third. The Bulgarian maintained his excellent start to the season, winning his second title of the year on home soil, defeating second seed, David Goffin, in straight sets in the final.<ref>{{cite web|title=Dimitrov Rules On Home Soil|url=https://www.atpworldtour.com/en/news/dimitrov-goffin-sofia-2017-sunday|website=www.atpworldtour.com|access-date=11 December 2017}}</ref> However, the Belgian managed to grab his first victory over Dimitrov, eliminating him in three sets in the quarterfinals of the [[2017 ABN AMRO World Tennis Tournament|Rotterdam Open]].

In March, Dimitrov played in the [[2017 BNP Paribas Open – Men's singles|Indian Wells Masters]], losing in three sets to Jack Sock in the third round, after missing four match points.<ref>{{cite web|title=Sock Saves 4MPs vs. Dimitrov|url=http://www.atpworldtour.com/en/news/nishikori-muller-indian-wells-2017-tuesday|publisher=atp.com|access-date=15 March 2017}}</ref> The Bulgarian then participated in the [[2017 Miami Open|Miami Open]], but was upset by unseeded [[Guido Pella]] in the second round.

Dimitrov began his clay-court season with a loss to [[Tommy Robredo]] in the second round of the [[2017 Grand Prix Hassan II – Singles|Grand Prix Hassan II]] tournament, for which he received a wildcard and was the top seed. This was followed by another upset at the [[2017 Monte-Carlo Rolex Masters – Singles|Monte-Carlo Masters]], where Dimitrov was seeded eighth and had a bye into the second round, but lost to qualifier [[Jan-Lennard Struff]].

The Bulgarian ended his losing streak in the [[2017 Mutua Madrid Open – Men's singles|Madrid Masters]], reaching the third round, where he was eliminated by Dominic Thiem in three tight sets after missing five match points in the third-set tiebreak.<ref>{{cite web|title=Thiem Saves 5 M.P. To Edge Dimitrov In Madrid|url=http://www.atpworldtour.com/en/news/thiem-dimitrov-madrid-2017-thursday|website=www.atpworldtour.com|access-date=7 December 2017}}</ref> Next, Dimitrov had a first-round exit in the [[2017 Italian Open – Men's singles|Rome Masters]], being defeated by [[Juan Martín del Potro]] in three sets. This was the fifth loss to the Argentine in five meetings. Dimitrov then went to the third round of the [[2017 French Open – Men's singles|French Open]], where he lost to [[Pablo Carreño Busta]].

Dimitrov started on grass court in [[2017 MercedesCup – Singles|Stuttgart]]. He was seeded second, but lost in his first match. The Bulgarian then had a good run at the [[2017 Aegon Championships – Singles|Queen's Club]] event, where he reached the semifinals. Dimitrov lost in three sets to in-form eventual champion Feliciano López. Without dropping a set, the Bulgarian reached the fourth round at [[2017 Wimbledon Championships – Men's singles|Wimbledon]], but then lost in straight sets to eventual champion Roger Federer in what was his sixth defeat in six official matches with the Swiss. Dimitrov returned to the top ten for the first time since February 2015 at the conclusion of the tournament.<ref>{{Cite web|title=Grigor Dimitrov &#124; Rankings History &#124; ATP Tour &#124; Tennis|url=https://www.atptour.com/en/players/grigor-dimitrov/d875/www.atptour.com/en/players/grigor-dimitrov/d875/overview|access-date=2021-11-23|website=ATP Tour}}</ref>

[[File:2017 Citi Open Tennis Grigor Dimitrov (35948754410).jpg|thumb|upright=.7|Dimitrov at the 2017 Washington Open]]
Dimitrov returned to hard courts in August. After reaching third rounds at the [[2017 Citi Open – Men's singles|Washington Open]] and the [[2017 Rogers Cup – Men's singles|Rogers Cup]] in Montreal, the Bulgarian won his first Masters 1000 title in [[2017 Western & Southern Open – Men's singles|Cincinnati]], defeating Nick Kyrgios in the final in straight sets, winning the tournament without losing a set. Dimitrov then reached the second round of the [[2017 US Open – Men's singles|US Open]], where he lost to teenager [[Andrey Rublev]].

In the beginning of October, Dimitrov reached the semifinals in [[2017 China Open – Men's singles|Beijing]] after wins over Juan Martín del Potro and Roberto Bautista Agut, and then the quarterfinals of the [[2017 Shanghai Rolex Masters|Shanghai Masters]]. In both events the Bulgarian was eliminated by world No. 1, Rafael Nadal, in three-setters.<ref>{{cite web|title=Rivalries of 2017: Nadal vs. Dimitrov|url=http://www.atpworldtour.com/en/news/best-rivalries-2017-nadal-dimitrov|website=www.atpworldtour.com|access-date=8 December 2017}}</ref> Dimitrov then advanced to the final of the [[2017 Stockholm Open|Stockholm Open]] with wins over Jerzy Janowicz, Mischa Zverev and Fabio Fognini but lost to US Open semifinalist del Potro in straight sets. This was Dimitrov's third final in Stockholm. In the following week, Dimitrov was confirmed to participate for the first time at the [[ATP Finals]], thus becoming the first Bulgarian to qualify for the season-ending championships.<ref name="ATP Finals">{{cite web|title=Dimitrov, Cilic Qualify For Nitto ATP Finals|url=http://www.atpworldtour.com/en/news/dimitrov-cilic-nitto-atp-finals-2017-qualify|website=atpworldtour.com|access-date=28 October 2017}}</ref>

Afterwards, he decided to skip the [[Vienna Open]] (despite being given a wildcard) due to fatigue, and to prepare for the [[Paris Masters]] the following week, where Dimitrov grabbed third victory in a row over Richard Gasquet before losing in the third round to big serving [[John Isner]] in three sets. On the following week, prior to the ATP Finals, Dimitrov achieved a new career high, climbing to world No. 6 position.

Dimitrov was drawn in the [[Pete Sampras]] group of the [[2017 ATP Finals – Singles|2017 ATP Finals]], together with Rafael Nadal, Dominic Thiem and David Goffin. Playing with Thiem in his debut match, Dimitrov clinched a maiden victory in the ATP Finals in a tight three-setter.<ref>{{cite web|title=DIMITROV TAKES LONDON DEBUT|url=http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-thiem-nitto-atp-finals-2017-monday-2|website=www.nittoatpfinals.com|access-date=13 November 2017|archive-date=13 November 2017|archive-url=https://web.archive.org/web/20171113222640/http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-thiem-nitto-atp-finals-2017-monday-2|url-status=dead}}</ref> The Bulgarian then routed Goffin, allowing only two games to his opponent. With this win Dimitrov won the first place in the group and secured his place at the semi-finals.<ref>{{cite web|title=DIMITROV ROUTS GOFFIN TO REACH SFS|url=http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-goffin-nitto-atp-finals-2017-wednesday|website=www.nittoatpfinals.com|access-date=15 November 2017|archive-date=16 November 2017|archive-url=https://web.archive.org/web/20171116015840/http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-goffin-nitto-atp-finals-2017-wednesday|url-status=dead}}</ref> Dimitrov stayed perfect in the group after another convincing victory, this time against alternate [[Pablo Carreño Busta]].<ref>{{cite web|title=DIMITROV FLIES INTO NITTO ATP FINALS SFS|url=http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-carreno-busta-nitto-atp-finals-2017-friday|website=www.nittoatpfinals.com|access-date=18 November 2017|archive-date=21 November 2017|archive-url=https://web.archive.org/web/20171121123702/http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-carreno-busta-nitto-atp-finals-2017-friday|url-status=dead}}</ref> The Bulgarian came back from a set down to ultimately eliminate in-form [[Jack Sock]] in the semi-finals.<ref>{{cite web|title=DIMITROV REMAINS UNBEATEN, REACHES NITTO ATP FINALS TITLE MATCH|url=http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-sock-nitto-atp-finals-2017-saturday-sf|website=www.nittoatpfinals.com|access-date=18 November 2017|archive-date=19 November 2017|archive-url=https://web.archive.org/web/20171119173410/http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-sock-nitto-atp-finals-2017-saturday-sf|url-status=dead}}</ref>
Dimitrov won the biggest title of his career by defeating once again David Goffin in three tight sets in the final. He finished the tournament as an undefeated champion, receiving a prize of $2,549,000 and 1,500 ranking points, the latter helped him finish 2017 at a career-high world No. 3 (only behind Nadal and Federer).<ref>{{cite web|title=DIMITROV WINS BIGGEST TITLE OF HIS CAREER|url=http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-goffin-nitto-atp-finals-2017-sunday-final|website=www.nittoatpfinals.com|access-date=19 November 2017|archive-date=20 November 2017|archive-url=https://web.archive.org/web/20171120143734/http://www.nittoatpfinals.com/en/news-and-media/tennis/dimitrov-goffin-nitto-atp-finals-2017-sunday-final|url-status=dead}}</ref>

Dimitrov ended his 2017 season with these significant milestones [current figure in brackets]: (1) [[2017 Western & Southern Open – Men's singles|first Masters 1000 title]] (2) [[2017 ATP Finals – Singles|first ATP Finals crown]], (3) [[Grigor Dimitrov career statistics#ATP career finals|5 Tour finals]], (4) [[Grigor Dimitrov career statistics#ATP career finals|four tour titles]], (5) [[Grigor Dimitrov career statistics#Top 10 wins|eight top-10 match wins]] [had 13 total prior to 2017], (6) 250 career match wins [[Grigor Dimitrov career statistics#Singles|[257 match wins]]], (7) cracked $10,000,000 in career earnings [[Grigor Dimitrov career statistics#ATP Tour career earnings|[$13,103,976]]], (8) cracked $5,000,000 in a single season [[Grigor Dimitrov career statistics#ATP Tour career earnings|[$5,628,512]]], (9) [[2017 Australian Open – Men's singles#Finals|second Grand Slam semifinal]], (10) [[2017 Australian Open – Men's singles#Finals|first Grand Slam semifinal on hard courts]].

===2018: Australian Open quarterfinal, 15th final, Laver Cup win===
[[File:Grigor Dimitrov (Bul) (24852347247) (cropped).jpg|thumb|right|upright=.7|Dimitrov at the [[2018 Australian Open]]]]
Dimitrov started his 2018 campaign in [[2018 Brisbane International|Brisbane]], where he was the defending champion and top seed. He started from the second round with hard three set win against the home favourite and wild card [[John Millman]], then overcame with another three setter the British number two [[Kyle Edmund]]. Dimitrov was eliminated in the semi-finals by the third seed and eventual champion Nick Kyrgios. The Bulgarian played in the doubles as well. Paired with [[Ryan Harrison]], he reached the semifinals, before withdrawing.
Having started his campaign at [[2018 Australian Open – Men's singles|Australian Open]] with a couple of wins against qualifiers Dennis Novak and Mackenzie McDonald, Dimitrov was drawn against Andrey Rublev who had knocked him out in the second round of US Open several months before and took revenge, eliminating the 30th seeded Russian. Dimitrov then edged in form Nick Kyrgios in tight four sets to qualify for his third Australian Open quarter-final, where he lost to Kyle Edmund in four sets.<ref>{{cite web|title=Dimitrov Praises Edmund, Searches For Silver Lining|url=http://www.atpworldtour.com/en/news/dimitrov-reaction-australian-open-2018-tuesday|publisher=ATP|access-date=24 February 2018}}</ref> In the following week Dimitrov stated that he had played the last matches with a shoulder injury. Failing to recover, the Bulgarian withdrew from the [[2018 Diema Xtra Sofia Open|Sofia Open]], where he was defending champion.

In February, Dimitrov reached the final of the [[2018 ABN AMRO World Tennis Tournament – Singles|Rotterdam Open]] without dropping a set, defeating [[Yūichi Sugita]], [[Filip Krajinović]], Andrey Rublev, and David Goffin en route, but eventually lost to Roger Federer, who would regain world No. 1 ranking after the tournament.<ref>{{cite web|title=Federer Breezes To Rotterdam Crown|url=http://www.atpworldtour.com/en/news/rotterdam-2018-final-dimitrov-federer|publisher=ATP|access-date=24 February 2018}}</ref> Next, Dimitrov played in [[2018 Dubai Tennis Championships – Men's singles|Dubai]], where he was top seed, but was upset in the first round by [[Malek Jaziri]].

In March, Dimitrov was third seed at both the [[2018 BNP Paribas Open – Men's singles|Indian Wells]] and [[2018 Miami Open – Men's singles|Miami]] Masters, but faced early eliminations by Fernando Verdasco in the second round and by [[Jérémy Chardy]] in the third round, respectively.

Dimitrov rebounded on the next tournament, the [[2018 Monte-Carlo Masters – Singles|Monte-Carlo Masters]], advancing to the semi-finals of the clay event after beating No. 10 David Goffin in the quarter-finals. Dimitrov ultimately lost to world No. 1 Rafael Nadal.<ref>{{cite news|title=Another Year, Another Monte-Carlo Final For Rafa|url=http://www.atpworldtour.com/en/news/nadal-dimitrov-monte-carlo-2018-saturday|access-date=21 April 2018|publisher=atpworldtour.com}}</ref> That was followed by a quarter-final in [[2018 Barcelona Open Banco Sabadell – Singles|Barcelona]], where Dimitrov lost to Pablo Carreño Busta. After the match ending handshake, Dimitrov accused Carreño Busta of stopping the point in the second set tie-break, which led to an unforced error by the Bulgarian. Carreño Busta denied the accusations.<ref>{{cite web|title=VIDEO: 'I'LL REMEMBER THIS'—DIMITROV RIPS CARRENO BUSTA AFTER NON-CALL|url=http://www.tennis.com/pro-game/2018/04/ill-remember-dimitrov-rips-carreno-busta-court/73539/|website=www.tennis.com|access-date=28 April 2018}}</ref>

In May, Dimitrov lost in the second rounds of the [[2018 Mutua Madrid Open – Men's singles|Madrid]] and [[2018 Italian Open – Men's singles|Rome]] Masters to Milos Raonic and Kei Nishikori, respectively. Dimitrov then lost in straight sets to Fernando Verdasco in the third round of the [[2018 French Open – Men's singles|French Open]].

Dimitrov had his worst grass-court season since 2010, having recorded early losses to Novak Djokovic at the [[2018 Queen's Club Championships – Singles|Queen's Club]] tournament and to Stan Wawrinka at the [[2018 Wimbledon Championships – Men's singles|Wimbledon Championships]]. The second of the defeats came in the first round of the Grand Slam event.

Dimitrov next played in August at the [[2018 Rogers Cup – Men's singles|Toronto Masters]], where he reached the quarterfinals, losing to Kevin Anderson. Dimitrov then failed to defend his Masters title in [[2018 Western & Southern Open – Men's singles|Cincinnati]] after he was beaten in the third round by the eventual champion Novak Djokovic in a tight three-setter. As a result, Dimitrov's ranking dropped to world No. 8. That was followed by first round elimination at the [[2018 US Open – Men's singles|2018 US Open]], with Dimitrov losing to Stan Wawrinka in straights.

Dimitrov contributed to Team Europe for winning the second edition of the [[2018 Laver Cup|Laver Cup]]. However his struggles with form continued after early exits at the China Open and in Vienna, losing to unseeded [[Dušan Lajović]] and Mikhail Kukushkin, respectively. Dimitrov's season ended after the Paris Masters, where he lost to fifth seed, Marin Čilić in the third round. Dimitrov didn't qualify for the ATP Finals, where he was the defending champion. Former world No. 1, [[Andre Agassi]], joined Dimitrov's team prior to the Paris Masters.<ref>{{cite news |title=GRIGOR DIMITROV CONFIRMS HE HAS ADDED ANDRE AGASSI TO HIS TEAM |url=http://www.tennis.com/pro-game/2018/10/grigor-dimitrov-confirms-he-has-added-andre-agassi-his-team/77793/ |access-date=23 January 2019 |publisher=tennis.com}}</ref>

===2019: Shoulder injury, US Open semifinal===
[[File:Dimitrov PM19 (6) (49308113042).jpg|thumb|upright=.7|right|Dimitrov at the [[2019 Rolex Paris Masters]]]]

Dimitrov started his campaign in Brisbane where he defeated [[Yoshihito Nishioka]] and [[John Millman]] in straight sets before losing to eventual champion Kei Nishikori in the quarterfinals.<ref>{{cite web|url=https://www.atptour.com/en/players/grigor-dimitrov/d875/player-activity|title = Grigor Dimitrov &#124; Player Activity|website=ATP Tour}}</ref> In January, Dimitrov reached the last 16 of the [[2019 Australian Open – Men's singles|2019 Australian Open]], but was knocked out by [[Frances Tiafoe]] in four sets.

Having suffered from a shoulder injury, Dimitrov returned to play in the [[2019 Miami Open – Men's singles|Miami Masters]], reaching the third round. Dimitrov then started his clay court campaign at the [[2019 Monte-Carlo Masters – Singles|Monte-Carlo Masters]], where he lost to Rafael Nadal in the third round. Dimitrov then went to the third round of [[2019 Barcelona Open Banco Sabadell – Singles|Barcelona Open]]. His ranking deteriorated to No. 49, the lowest since 2012. At the [[2019 French Open – Men's singles|French Open]], Dimitrov upset Marin Čilić in the second round but was subsequently eliminated by Stan Wawrinka in straight sets.<ref>{{cite web|url=http://www.atptour.com/en/news/dimitrov-cilic-wawrinka-roland-garros-2019-wednesday|title=Dimitrov Returns To Form, Beats Cilic In Five Sets|date=2019-05-21|website=ATP Tour|access-date=2019-06-01}}</ref> Dimitrov had a disappointing [[2019 Wimbledon Championships – Men's singles|Wimbledon]], losing to [[Corentin Moutet]] in five sets in the first round, despite being up two sets.

Dimitrov's hard court season started off poorly. He lost in the first round of the [[2019 BB&T Atlanta Open|Atlanta Open]] to world No. 405 [[Kevin King (tennis)|Kevin King]], who had never won a main-draw match on the ATP Tour.<ref>{{cite web |last1=Eichenholz |first1=Andrew |title=World No. 405 King Stuns Dimitrov In Atlanta For First ATP Tour Win |url=https://www.atptour.com/en/news/king-dimitrov-atlanta-2019-tuesday |website=ATP Tour |publisher=ATP Tour, Inc. |access-date=12 September 2019}}</ref><ref>{{cite web |title='Upset of the year': World No.405 compounds former prodigy's fall from grace |url=https://au.sports.yahoo.com/atlanta-open-grigor-dimitrov-fall-from-grace-kevin-king-upset-080413866.html |website=Yahoo Sport Australia |date=24 July 2019 |access-date=12 September 2019}}</ref> Dimitrov then lost to Stan Wawrinka in the first rounds of both the [[2019 Rogers Cup – Men's singles|Rogers Cup]] and the [[2019 Western & Southern Open – Men's singles|Western & Southern Open]]. Following this, Dimitrov had lost seven of his past eight matches, and his ranking had slipped to No. 78, his lowest ranking in over seven years.

At the [[2019 US Open – Men's singles|US Open]], Dimitrov was unseeded. He defeated [[Andreas Seppi]] in the first round before receiving a walkover over 12th seed [[Borna Ćorić]]. He then defeated lucky loser [[Kamil Majchrzak]] and [[Alex de Minaur]] in straight sets to reach the quarterfinals. There, he faced third seed Roger Federer. In a lengthy five-set match, Dimitrov upset Federer to reach his first Grand Slam semifinal since the 2017 Australian Open. This was also his first career win against Federer, having been defeated on seven previous occasions. He then lost to [[Daniil Medvedev]] in the semifinals. As a result of this run, Dimitrov rose 53 ranking places in a single tournament, appearing at World No. 25 the next week.

Dimitrov failed to proceed beyond the second round at [[2019 Chengdu Open|Chengdu]], [[2019 China Open (tennis)|Beijing]], [[2019 Stockholm Open|Stockholm]], and [[2019 Erste Bank Open|Vienna]]. At the [[2019 Rolex Paris Masters|Paris Masters]], he defeated [[Ugo Humbert]] and 12th seed David Goffin to reach the third round, where he defeated the fifth seed Dominic Thiem. In the quarterfinals, he defeated [[Cristian Garín]], before losing to Djokovic in straight sets in the semifinals.

===2020: Inaugural ATP Cup captain, French Open fourth round===
In January, Dimitrov participated and led as captain the Bulgarian team in the inaugural [[2020 ATP Cup]] where the top 24 countries qualified based on the singles ATP ranking of their No. 1 country player.<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-inspiring-bulgaria-feature-atp-cup-2020|title = Why Unity Will be 'Most Powerful Weapon' for Grigor Dimitrov'-Led Team Bulgaria|website=ATP Tour}}</ref> The Bulgarian team was No. 19 based on Dimitrov's ranking and part of Group C where Dimitrov won both his single matches against the top players of Great Britain, Dan Evans, and Moldova, [[Radu Albot]].<ref>{{cite web|url=https://www.atptour.com/en/news/bulgaria-moldova-atp-cup-2020-sunday|title = ATP Cup: Grigor Dimitrov Delivers! Bulgaria Beats Moldova in Sydney|website=ATP Tour}}</ref> He pulled a victory in doubles where as the underdogs he and teammate [[Alexandar Lazarov]] stunned the top British experienced pair of [[Jamie Murray]]/[[Joe Salisbury]] in a close three sets match.<ref>{{cite web|url=https://www.atptour.com/en/news/bulgaria-great-britain-atp-cup-2020-friday|title= Bulgarian Bench Clearing! Underdogs Stun Great Britain|website=ATP Tour}}</ref><ref>{{cite web|url= https://www.eurosport.com/tennis/atp-cup/2020/atp-cup-news-gb-fall-to-grigor-dimitrov-inspired-bulgaria-in-near-3am-finish_sto7595083/story.shtml|title=Great Britain fall to Dimitrov-inspired Bulgaria in near 3am finish|website=Eurosport|date=3 January 2020}}</ref>

In October, Dimitrov reached the fourth round of the [[2020 French Open|French Open]] for the first time, defeating [[Roberto Carballés Baena]], where he lost to [[Stefanos Tsitsipas]] in straight sets.<ref>{{cite web | url=https://www.atptour.com/en/news/carballes-baena-shapovalov-dimitrov-roland-garros-2020-thursday | title=Carballes Baena Upsets Shapovalov in Fifth Set for Series of Firsts at Roland Garros|website=ATP Tour }}</ref><ref>{{cite web|url=https://www.tennisworldusa.org/tennis/news/Tennis_Interviews/91967/stefanos-tsitsipas-speaks-highly-of-grigor-dimitrov-after-win-at-french-open/|title=Stefanos Tsitsipas speaks highly of Grigor Dimitrov after win at French Open|date=6 October 2020 }}</ref>

He finished the year in the top 20 for the fifth year in a row, ranked world No. 19.

===2021: Australian Open quarterfinal, Indian Wells semifinal===
In February, Dimitrov seeded 18th reached his fourth quarterfinal at the [[2021 Australian Open – Men's singles|Australian Open]], defeating former Grand Slam champion Marin Čilić in the first round, [[Alex Bolt]], 15th seed Pablo Carreño Busta by retirement and third seed and the previous year's runner-up Dominic Thiem in the fourth round, before losing to qualifier [[Aslan Karatsev]] after suffering from back spasms.<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-reaction-australian-open-2021-tuesday|title = Grigor Dimitrov: 'I Don't Like Quitting' – 2021 Australian Open Match Reaction &#124; ATP Tour &#124; Tennis}}</ref>

Dimitrov retired in the first round of the [[2021 French Open – Men's singles|French Open]] against [[Marcos Giron]] for the same reasons as a result of his back problems, after failing to convert three match points in the third set.<ref>{{cite web |url=https://www.essentiallysports.com/atp-tennis-news-unfortunate-grigor-dimitrov-forced-to-retire-from-1st-round-of-french-open-2021/ |title='UNFORTUNATE': Grigor Dimitrov Forced to Retire from 1st Round of French Open 2021|date = 30 May 2021}}</ref> Seeded 18th at the [[2021 Wimbledon Championships]], he lost to [[Alexander Bublik]] in the second round in three straight sets with two tiebreaks after Bublik hit 34 aces against Dimitrov.<ref>{{Cite news |url=https://www.nytimes.com/2021/07/02/sports/tennis/wimbledon-alexander-bublik.html |title=Who Needs Practice? Not Alexander Bublik |newspaper=The New York Times |date=2 July 2021 |last1=Rothenberg |first1=Ben}}</ref><ref>{{Cite web |url=https://www.wimbledon.com/en_GB/news/articles/2021-07-02/bublik_aceing_his_best_year_yet.html |title=Bublik aceing his best year yet |date=2 July 2021 |access-date=2021-11-23 |website=www.wimbledon.com}}</ref> He took his revenge by defeating Bublik at the [[2021 Western & Southern Open]] Masters in Cincinnati to reach the round of 16. He lost to Daniil Medvedev in straight sets.<ref>{{Cite web|title=Daniil Medvedev Marches Into Cincinnati QFs &#124; ATP Tour &#124; Tennis|url=https://www.atptour.com/en/news/www.atptour.com/en/news/medvedev-dimitrov-cincinnati-2021-thursday|access-date=2021-11-23|website=ATP Tour}}</ref> At the [[2021 US Open – Men's singles|US Open]], he retired with a foot injury after losing the first two sets to [[Alexei Popyrin]] in the second round.<ref>{{cite web |url=https://www.espn.com/tennis/story/_/id/32128596/us-open-australian-alexei-popyrin-ousts-grigor-dimitrov|access-date=29 September 2021|title=Aussie Alexei Popyrin ousts Grigor Dimitrov from US Open|date=September 2021}}</ref> He dropped out of the top 25, since he could not defend his points from the 2019 US Open semifinal, to No. 29 on 13 September 2021.

In late September, Dimitrov recorded his first win over Márton Fucsovics in three ATP head-to-head meetings at the [[2021 San Diego Open]] to reach the second round.<ref>{{Cite web|title=Dimitrov Sets Auger-Aliassime Clash In San Diego &#124; ATP Tour &#124; Tennis|url=https://www.atptour.com/en/news/www.atptour.com/en/news/dimitrov-fucsovics-san-diego-2021-tuesday|access-date=2021-11-23|website=ATP Tour}}</ref> He then won in the second round defeating ATP Tour debutant and lucky loser [[August Holmgren (tennis)]], after [[Félix Auger-Aliassime]] withdrawal, in straight sets 6–1, 6–1 in a 56 minutes match to reach his fifth quarterfinal of the season.<ref>{{Cite web|title=Aslan Karatsev Ousts Hubert Hurkacz In Battle Of Turin Contenders &#124; ATP Tour &#124; Tennis|url=https://www.atptour.com/en/news/www.atptour.com/en/news/karatsev-hurkacz-san-diego-2021-thursday|access-date=2021-11-23|website=ATP Tour}}</ref><ref>{{cite web|url=https://tennisuptodate.com/atp/dimitrov-cruises-through-to-san-diego-quarterfinals-following-auger-aliassime-withdrawal |title=Dimitrov cruises through to San Diego quarterfinals following Auger-Aliassime withdrawal |publisher=Tennisuptodate.com |date=2021-09-23 |accessdate=2021-11-23}}</ref> He reached his first semifinal of the year defeating Aslan Karatsev in three sets and taking his revenge for his earlier in the year loss at the AO.<ref>{{cite web|url=http://www.tennisnow.com/News/2021/October/Dimitrov-Reaches-First-Semifinal-of-2021-to-Set-Ru.aspx |title=Dimitrov Reaches First Semifinal of 2021 to Set Ruud Clash in San Diego |publisher=Tennis Now |date=2021-10-01 |accessdate=2021-11-23}}</ref> In the semifinals, he lost to eventual champion [[Casper Ruud]].<ref>{{Cite web|title=Casper Ruud Defeats Grigor Dimitrov San Diego Semi-finals 2021 &#124; ATP Tour &#124; Tennis|url=https://www.atptour.com/en/news/www.atptour.com/en/news/ruud-defeats-dimitrov-san-diego-semi-finals-2021|access-date=2021-11-23|website=ATP Tour}}</ref>

At [[2021 BNP Paribas Open|Indian Wells]], Dimitrov reached the round of 16 for the first time in his career, defeating en route qualifier [[Daniel Altmaier]] and then-world No. 20 and 16th seed [[Reilly Opelka]] in straight sets with no breaks, taking his revenge for his earlier in the year loss to the American at the [[2021 National Bank Open|Canadian Open]].<ref>{{Cite web|title=Grigor Dimitrov Gains Reilly Opelka Revenge In Indian Wells &#124; ATP Tour &#124; Tennis|url=https://www.atptour.com/en/news/www.atptour.com/en/news/dimitrov-indian-wells-2021-monday|access-date=2021-11-23|website=ATP Tour}}</ref><ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-masters-the-autumn-wind-to-defeat-reilly-opelka |title=Grigor Dimitrov masters the autumn wind to defeat Reilly Opelka at Indian Wells |publisher=Tennis.com |date= |accessdate=2021-11-23}}</ref> In the fourth round, Dimitrov defeated world No. 2 and top seed Daniil Medvedev 4–6, 6–4, 6–3 to reach the quarterfinals. He came back from a set and a double-break down at 4–6, 1–4 to eliminate the reigning [[2021 US Open – Men's singles|US Open]] champion and earn his first win over a top 2 opponent since 2016.<ref>{{cite web|url=https://www.atptour.com/en/news/medvedev-dimitrov-indian-wells-2021-wednesday|title=Dimitrov Roars Back in Indian Wells, Shocks Medvedev To Reach QFs|website=ATP Tour}}</ref> In the quarterfinals, he defeated eighth seed [[Hubert Hurkacz]] rallying again from a set down to reach the semifinals for the first time in his career at this Masters.<ref>{{Cite web|title=Grigor Dimitrov Downs Hubert Hurkacz, Moves Into Indian Wells SFs &#124; ATP Tour &#124; Tennis|url=https://www.atptour.com/en/news/www.atptour.com/en/news/hurkacz-dimitrov-indian-wells-2021-thursday|access-date=2021-11-23|website=ATP Tour}}</ref> He then lost to Cameron Norrie in the semi-finals.

At the [[2021 Rolex Paris Masters|Paris Masters]], he defeated wildcard Richard Gasquet and 2018 champion Karen Khachanov in the second round, with the last set being 6–0. He lost to fourth seed Alexander Zverev in the round of 16.

===2022: 350th career win, Masters semifinal, 30th Top 10 win===
[[File:Dimitrov MCM22 (81) (52035377642).jpg|thumb|right|upright=.7|Dimitrov at the [[2022 Monte-Carlo Masters]]]]
The season for Dimitrov began at the [[2022 Melbourne Summer Set 1 – Men's singles|Melbourne Summer Set]] tournament, where he reached the semifinals, before losing to qualifier [[Maxime Cressy]]. Next, he participated in the [[2022 Australian Open – Men's singles|Australian Open]] but he lost in the second round to [[Benoît Paire]].<ref>{{cite web |url=https://ausopen.com/players/bulgaria/grigor-dimitrov#!matches|access-date=14 April 2022|title=Grigor Dimitrov Australian Open Profile|date=January 2022}}</ref>
At the [[2022 Delray Beach Open]] following his second round win over [[Mitchell Krueger]],<ref>{{Cite web | url=https://www.atptour.com/en/news/dimitrov-krueger-delray-2022-thursday | title=Grigor Dimitrov Returns with Win in Tough Delray Beach Conditions|website=ATP Tour }}</ref> Dimitrov became only the second man born in the ‘90s or later to reach 350 career wins, after Milos Raonic. He was the 130th man in the Open Era and the 22nd active player to do it.<ref>{{Cite web | url=https://www.tennis.com/baseline/articles/stat-of-the-day-grigor-dimitrov-350th-career-win-delray-beach | title=Stat of the Day: Grigor Dimitrov records 350th tour-level win of career }}</ref>

In March, Dimitrov reached the quarterfinals of the [[2022 BNP Paribas Open – Men's singles|Indian Wells Masters]] before losing to seventh seed Andrey Rublev in straight sets. At the [[2022 Monte-Carlo Masters – Singles|Monte-Carlo Masters]], he reached the semifinals with an upset against fourth seed Casper Ruud<ref>{{cite web |url=http://www.tennisnow.com/News/2022/April/Dimitrov-Upsets-Ruud,-Fritz-Fends-Off-Korda-in-Mon.aspx|access-date=14 April 2022|title=Dimitrov Upsets Ruud, Fritz Fends Off Korda in Monte-Carlo|date=14 April 2022}}</ref> and again 11th seed [[Hubert Hurkacz]].<ref>{{Cite web | url=https://www.atptour.com/en/news/dimitrov-hurkacz-monte-carlo-2022-friday | title=Grigor Dimitrov Downs Hubert Hurkacz for Semi-Final Spot|website=ATP Tour }}</ref> At the [[2022 French Open – Men's singles|French Open]], he lost in the third round to 15th seed [[Diego Schwartzman]] in straight sets, whom Dimitrov defeated also in straight sets at the [[2022 Mutua Madrid Open|Madrid Open]].<ref>{{cite web | url=https://www.atptour.com/en/news/schwartzman-dimitrov-roland-garros-2022-friday | title=Diego Schwartzman Dispatches Grigor Dimitrov, Gains Revenge at Roland Garros|website=ATP Tour }}</ref> At [[2022 Wimbledon Championships|Wimbledon]], he retired in the first round against [[Steve Johnson (tennis)|Steve Johnson]].

At the [[2022 National Bank Open|Canadian Open]], he reached the second round in singles and in doubles with Andrey Rublev defeating Canadian wildcard debutant [[Alexis Galarneau]] and Wimbledon doubles champions Ebden/Purcell respectively.<ref>{{cite web | url=https://www.atptour.com/en/news/dimitrov-rublev-montreal-2022-tuesday-doubles | title=Grigor Dimitrov & Andrey Rublev Upset Wimbledon Doubles Champions in Montreal|website=ATP Tour }}</ref> The pair also reached the second round of the [[2022 Western & Southern Open]] defeating Dan Evans and [[John Peers]].<ref>{{cite web | url=https://www.atptour.com/en/news/dimitrov-rublev-cincinnanti-2022-doubles-wednesday | title=Grigor Dimitrov & Andrey Rublev Win Cincinnati Doubles Opener|website=ATP Tour }}</ref> Following two straight first-round losses at the [[2022 Sofia Open]] and the [[2022 Stockholm Open]], he won his opening match at the [[2022 Erste Bank Open]] in Vienna against [[Thiago Monteiro (tennis)|Thiago Monteiro]].<ref>{{cite web | url=https://www.atptour.com/en/news/dimitrov-vienna-2022-tuesday | title=Grigor Dimitrov Earns Opening Win in Vienna|website=ATP Tour }}</ref> Next he defeated world No. 8 and third seed Andrey Rublev (his 30th top-10 win) to reach the quarterfinals<ref>{{cite news | url=https://www.reuters.com/lifestyle/sports/atp-roundup-stefanos-tsitsipas-falls-vienna-2022-10-28/ | title=ATP roundup: Stefanos Tsitsipas falls in Vienna | agency=Reuters | date=28 October 2022 |website=ATP Tour}}</ref><ref>{{cite web | url=https://www.atptour.com/en/news/medvedev-thiem-vienna-2022-thursday | title=Daniil Medvedev Tames Dominic Thiem in Vienna }}</ref> and [[Marcos Giron]] to reach his third semifinal of the season. He lost to world No. 4 and top seed eventual champion, Daniil Medvedev, in straight sets.<ref>{{cite web | url=https://www.atptour.com/en/news/medvedev-dimitrov-vienna-2022-saturday | title=Daniil Medvedev Marches into Vienna Final|website=ATP Tour }}</ref> At the [[2022 Rolex Paris Masters]] he reached the third round defeating [[Botic van de Zandschulp]], lucky loser Fabio Fognini, before losing to world No. 1, [[Carlos Alcaraz]], to end his season.<ref>{{cite web | url=https://m.tennis24.bg/new.php?id=66150 | title=Григор Димитров загуби от световния №1 в последния си двубой за сезона }}</ref><ref>{{cite web | url=https://www.atptour.com/en/news/alcaraz-dimitrov-paris-2022-thursday | title=Carlos Alcaraz Races Past Grigor Dimitrov to Paris QFS |website=ATP Tour}}</ref>

He finished the year in the top 30 for the tenth year in a row, ranked world No. 28 on 21 November 2022. Based on this ranking, being the Bulgarian male player No. 1, he was confirmed two days later as a participant at the [[2023 United Cup]] as part of the Bulgarian team.<ref>{{cite web | url=https://www.atptour.com/en/news/united-cup-field-set | title=United Cup Field Set|website=ATP Tour }}</ref><ref>{{cite web | url=https://www.unitedcup.com/en/news/bulgaria-and-kazakhstan-complete-united-cup-field | title=Bulgaria and Kazakhstan Complete United Cup Field &#124; United Cup &#124; Tennis | access-date=24 November 2022 | archive-date=2 December 2022 | archive-url=https://web.archive.org/web/20221202091929/https://www.unitedcup.com/en/news/bulgaria-and-kazakhstan-complete-united-cup-field | url-status=dead }}</ref>

===2023: Inaugural United Cup, 400th win & return to the top 15===
Dimitrov reached the third round at the [[2023 Australian Open]] defeating Aslan Karatsev and [[Laslo Djere]] before losing in straight sets to eventual champion Novak Djokovic, who went on to win his 10th Australian Open and 22nd Grand Slam.<ref>{{cite web | url=https://www.atptour.com/en/news/djokovic-dimitrov-australian-open-2023-saturday | title=Novak Djokovic Defeats Grigor Dimitrov at Australian Open 2023|website=ATP Tour}}</ref>

At the [[2023 ABN AMRO Open|Rotterdam Open]], he defeated again Karatsev in 59 minutes to reach the second round.<ref>{{cite web | url=https://www.atptour.com/en/news/dimitrov-karatsev-rotterdam-2023-monday | title=Dimitrov, Wawrinka Win Rotterdam Openers|website=ATP Tour }}</ref> Next he defeated world No. 10 and fifth seed Hubert Hurkacz in straight sets to reach the quarterfinals. He reached his 43rd career semifinal defeating Alex de Minaur in three sets and first since 2018 at this tournament.<ref>{{cite web | url=https://www.tennismajors.com/atp/rotterdam-open-dimitrov-makes-semi-finals-661253.html | title=Rotterdam Open: Dimitrov ruins de Minaur birthday party | date=17 February 2023|website=ATP Tour }}</ref><ref>{{cite web |title=Hot Shots: Iga Świątek dominates in Doha, Grigor Dimitrov flirts with Rotterdam trophy |url=https://www.usopen.org/en_US/news/articles/2023-02-17/hot_shots_iga_swiatek_dominates_in_doha_grigor_dimitrov_flirts_with_rotterdam_trophy.html |website=[[US Open (tennis)|US Open]] |date=2023-02-17 |archive-url=https://web.archive.org/web/20230217211555/https://www.usopen.org/en_US/news/articles/2023-02-17/hot_shots_iga_swiatek_dominates_in_doha_grigor_dimitrov_flirts_with_rotterdam_trophy.html |archive-date=2023-02-17 |url-status=live |last1=Kapetanakis |first1=Arthur}}</ref><ref>{{cite web | url=https://dsport.bg/na-zivo-grigor-dimitrov-aleks-de-minor~109628.html | title=Григор развали празника на Демона, спаси два мачбола и е на полуфинал в Ротердам! – Тенис – Dsport.bg | date=17 February 2023 }}</ref> As a result, he returned to the top 25 in the rankings. He lost to world No. 11 and sixth seed [[Daniil Medvedev]] in straight sets.<ref>{{cite web | url=https://www.atptour.com/en/news/medvedev-dimitrov-rotterdam-2023-saturday | title=Medvedev Sees off Dimitrov for Rotterdam Final Berth|website=ATP Tour }}</ref>

At the [[2023 BNP Paribas Open]], he lost in the second round (having received a bye) to [[Jason Kubler]] after retirement with a right-knee injury in the third set.<ref>{{cite web | url=https://www.atptour.com/en/news/rublev-lehecka-tiafoe-giron-indian-wells-2023-Friday | title='Grateful' Rublev Rides Crowd Support to Lehecka Revenge in Indian Wells|website=ATP Tour }}</ref> In [[2023 Miami Open|Miami]] he won his second round match against qualifier [[Jan-Lennard Struff]].

In [[2023 Monte-Carlo Masters|Monte-Carlo]], he won in the first round over [[Ben Shelton (tennis)|Ben Shelton]]<ref>{{cite web | url=https://www.atptour.com/en/news/dimitrov-monte-carlo-2023-tuesday | title=Dimitrov Defeats Shelton in Monte-Carlo|website=ATP Tour }}</ref> before losing to [[Jiří Lehečka]].<ref>{{cite tweet|url=https://x.com/TennisTV/status/1646138892440186881 |title= Lehecka's 2023 aging like a fine wine 🍷@jirilehecka takes out last year's semi-finalist Dimitrov 7-6(4) 6-4 in Monte Carlo! #RolexMonteCarloMasters| number= 1646138892440186881 |user=TennisTV|date=12 April 2023}}</ref> As a result, he dropped outside of the top 30 on 17 April 2023 in the rankings being unable to defend his semifinal points from the previous year. In [[2023 Mutua Madrid Open|Madrid]] he defeated [[Grégoire Barrère]] in the second round before losing to top seed Carlos Alcaraz. In [[2023 Italian Open (tennis)|Rome]], he defeated Stan Wawrinka in the second round,<ref>{{cite news|title=Italian Open |website=eurosport.co.uk | url=https://www.eurosport.co.uk/tennis/atp-rome/2023/rome-masters-british-no.-1-cameron-norrie-and-home-favourite-jannik-sinner-storm-into-last-16-with-c_sto9601717/story.shtml | access-date=26 June 2023}}</ref> before also losing to the top seed, world No. 1 Novak Djokovic.

In [[2023 Geneva Open|Geneva]], he won his first two rounds matches against [[Roberto Carballés Baena]] and [[Christopher O'Connell]] to reach the semifinals.<ref>{{cite web | url=https://www.atptour.com/en/news/fritz-ivashka-geneva-2023-thursday | title=Jarry Upsets Ruud, Reaches Geneva SFS |website=ATP Tour}}</ref> 
He reached his first final since 2018 defeating second seed and top-10 player [[Taylor Fritz]]<ref>{{cite web | url=https://www.atptour.com/en/news/geneva-2023-friday | title=Grigor Dimitrov Reaches Geneva Final &#124; ATP Tour &#124; Tennis }}</ref> before losing in the final to [[Nicolás Jarry]].<ref>{{cite web | url=https://www.atptour.com/en/news/dimitrov-jarry-geneva-2023-final-saturday | title=Nicolas Jarry Wins Geneva Title, Defeats Grigor Dimitrov|website=ATP Tour}}</ref> Dimitrov reached the fourth round at [[2023 French Open|Roland Garros]] for the second time at this major, defeating qualifier [[Timofey Skatov]], [[Emil Ruusuvuori]] and Daniel Altmaier without losing a set.<ref>{{cite tweet|user=ATPMediaInfo|number=1665108921260945408|title=@GrigorDimitrov defeats Altmaier 6–4 6–3 6–1 and advances to the 4R @rolandgarros for 2nd time (2020) in 13 appearances. This is the Bulgarian's 13th #GrandSlam 4R in 50 tournaments}}</ref> He lost to 22nd seed [[Alexander Zverev]] in straight sets.

He qualified for the main draw at the [[2023 Queen's Club Championships]] and reached the quarterfinals also without dropping a set, defeating eight seed [[Francisco Cerundolo]].<ref>{{cite web | url=https://www.atptour.com/en/news/alcaraz-lehecka-london-2023-thursday | title=Carlos Alcaraz Bounces Back with Dominant Win to Reach Queen's Club QFS|website=ATP Tour}}</ref> He lost to top seed and world No. 2, Carlos Alcaraz, in straight sets.<ref>{{cite web | url=https://www.atptour.com/en/news/alcaraz-dimitrov-queens-2023-qf | title=Alcaraz Extends Best Grass Run with Queen's Club QF Win|website=ATP Tour}}</ref> His good form continued at the [[2023 Wimbledon Championships]] reaching the fourth round without losing a set, defeating top 10 player Frances Tiafoe, before losing to world No. 6, [[Holger Rune]]. He returned to the top 20 on 24 July 2023.

In the beginning of the North American Summer swing, seeded fifth, he reached the semifinals at the [[2023 Citi Open|Washington Open]]<ref>{{Cite web |last=Anirudh |date=2023-08-02 |title="I'm not a spring chicken anymore" – Grigor Dimitrov on beating Mackenzie McDonald at Citi Open in Washington |url=https://www.sportskeeda.com/tennis/news-i-m-spring-chicken-anymore-grigor-dimitrov-beating-mackenzie-mcdonald-citi-open-washington |access-date=2023-11-15 |website=www.sportskeeda.com |language=en-us}}</ref> after a walkover from [[Ugo Humbert]], before losing to eventual champion Dan Evans.<ref>{{Cite news |title=Evans beats Dimitrov to reach first ATP 500 final |language=en-GB |work=BBC Sport |url=https://www.bbc.com/sport/tennis/66420458 |access-date=2023-11-15}}</ref> At the [[2023 US Open (tennis)|US Open]] he reached the second round, defeating [[Alex Molcan]] after coming from a two sets to love down deficit for the first time in his career, saving three match balls, in five sets with three tiebreaks, in a match lasting close to 4 hours and 40 minutes, the longest of the day.<ref name=USOpenGrigorDimitrov2023>{{cite web |url=https://www.usopen.org/en_US/news/articles/2023-08-29/by_the_numbers_facts_and_figures_from_round_1_at_the_2023_us_open.html |title=By the numbers: Facts and figures from Round 1 at the 2023 US Open |publisher=US Open |last=Oddo |first=Chris |date=29 August 2023 |access-date=22 January 2024}}</ref><ref>{{cite web | title=Григор започна с три спасени мачбола и изумителен маратонски обрат на US Open |publisher=sportal.bg|url=https://sportal.bg/news-2023082913015982021|date=30 August 2023|accessdate=31 August 2023}}</ref><ref>{{Cite web |title=Dimitrov Denies Match Points to Set Up US Open Match vs. Murray – Tennis Now |url=https://www.tennisnow.com/News/2023/August/Dimitrov-Denies-Match-Points-to-Set-Up-US-Open-Mat.aspx |access-date=2023-11-15 |website=www.tennisnow.com}}</ref> Next he reached the third round defeating Andy Murray, before losing to Alexander Zverev, his third straight loss to the German in the season.<ref>{{cite web |url=https://www.usopen.org/en_US/news/articles/2023-09-02/alexander_zverev_ousts_grigor_dimitrov_at_the_2023_us_open.html |title=Alexander Zverev ousts Grigor Dimitrov at the 2023 US Open |publisher=US Open |last=Sode |first=Scott |date=2 September 2023 |access-date=22 January 2024}}</ref>

He recorded his 400th career win at the [[2023 Chengdu Open]] defeating [[Juan Pablo Varillas]] becoming the first man born in the 1990 or later to hit that milestone and the tenth active men's player.<ref>{{Cite web |title='I've Lived For The Game': Grigor Dimitrov Reflects On 400th Win {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/dimitrov-400-wins-chengdu-2023 |access-date=2023-11-15 |website=ATP Tour}}</ref><ref>{{Cite web |last= |title=Stat of the Day: Grigor Dimitrov records milestone 400th win of career in Chengdu |url=https://www.tennis.com/news/articles/stat-of-the-day-grigor-dimitrov-records-milestone-400th-win-of-career-in-chengdu |access-date=2023-11-15 |website=Tennis.com |language=en}}</ref><ref>{{Cite web |title=Alexander Zverev Defeats Pavel Kotov, Girgor Dimitrov Hits 400 In Chengdu {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/dimitrov-chengdu-2023-saturday |access-date=2023-11-15 |website=ATP Tour}}</ref><ref>{{Cite web |date=2023-09-24 |title="It only motivates me more" – Dimitrov on 400 wins |url=https://www.tennismajors.com/atp/it-not-only-motivates-me-to-play-well-but-to-develop-more-dimitrov-on-reaching-the-400-win-mark-716214.html |access-date=2023-11-15 |website=Tennis Majors |language=en-US}}</ref> He reached the semifinals defeating Christopher O'Connell.<ref>{{Cite web |title=Lorenzo Musetti Seals SF Spot In Chengdu {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/musetti-zverev-chengdu-2023-sunday |access-date=2023-11-15 |website=ATP Tour}}</ref> He lost to Alexander Zverev for a seventh consecutive time (fourth straight season loss), in straight sets. In the next tournament, the [[2023 China Open (tennis)|China Open]] of the Asian swing, he came back from a 2–6, 1–5 deficit, for a second time in the season, and won his first-round match against wildcard [[Mackenzie McDonald]].<ref>{{Cite web |date=2023-09-29 |title=Dimitrov recovers to edge past McDonald and into the second round |url=https://www.tennismajors.com/atp/china-open-dimitrov-moves-into-second-round-717141.html |access-date=2023-11-15 |website=Tennis Majors |language=en-US}}</ref> Next, he defeated third seed Holger Rune for his fourth top 10 win (the most since the 2017 season), to reach the quarterfinals of this tournament for the fourth time in eight appearances.<ref>{{Cite web |title=Jannik Sinner Beats Yoshihito Nishioka To Reach Beijing QFs {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/sinner-nishioka-rune-dimitrov-beijing-2023-sunday |access-date=2023-11-15 |website=ATP Tour}}</ref>

At [[2023 Rolex Shanghai Masters|Shanghai]], he reached the fourth round defeating 13th seed [[Karen Khachanov]].<ref>{{Cite web |title=Tommy Paul Boosts Turin Hopes, Grigor Dimitrov Advances In Shanghai {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/paul-fils-dimitrov-shanghai-2023-monday |access-date=2023-11-15 |website=ATP Tour}}</ref> Next he defeated world No. 2 and top seed Carlos Alcaraz to reach the quarterfinals of a Masters 1000 for the first time in the season and only the second time at this Masters.<ref>{{Cite web |title=Grigor Dimitrov Beats Carlos Alcaraz In Shanghai {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/alcaraz-dimitrov-shanghai-2023-wednesday |access-date=2023-11-15 |website=ATP Tour}}</ref><ref>{{Cite web |last= |title="I'm still here": Grigor Dimitrov topples Carlos Alcaraz for first time in Shanghai |url=https://www.tennis.com/news/articles/im-still-here-grigor-dimitrov-topples-carlos-alcaraz-for-first-time-in-shanghai |access-date=2023-11-15 |website=Tennis.com |language=en}}</ref> He defeated Nicolás Jarry and reached his first Masters semifinal since the 2022 Monte-Carlo Masters.<ref>{{Cite web |title=Grigor Dimitrov Beats Nicolas Jarry For Shanghai SF Berth {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/dimitrov-jarry-shanghai-2023-friday-qf |access-date=2023-11-15 |website=ATP Tour}}</ref><ref>{{Cite web |last= |title=Grigor Dimitrov's semifinal run in Shanghai is a good time to notice he's having one of his best seasons |url=https://www.tennis.com/news/articles/grigor-dimitrov-semifinal-shanghai-rolex-masters |access-date=2023-11-15 |website=Tennis.com |language=en}}</ref> He lost to sixth seed Andrey Rublev.<ref>{{Cite web |title=Andrey Rublev Beats Grigor Dimitrov, Sets Hubert Hurkacz Final In Shanghai {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/rublev-dimitrov-shanghai-2023-saturday-sf |access-date=2023-11-15 |website=ATP Tour}}</ref> He continued his good form on the European indoor hardcourts in [[2023 Erste Bank Open|Vienna]] and defeated [[Lorenzo Musetti]] in straight sets in the first round but lost to top seed Daniil Medvedev in the second in three sets.<ref>{{Cite web |title=Daniil Medvedev Beats Grigor Dimitrov In Vienna {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/medvedev-dimitrov-rublev-arnaldi-vienna-2023-thursday |access-date=2023-11-15 |website=ATP Tour}}</ref> At the next Masters in [[2023 Rolex Paris Masters|Paris]] he reached again the round of 16 defeating world No. 3 Medvedev this time, winning at the seventh match point, his third top-5 win within a month<ref>{{Cite web |last= |title=Grigor Dimitrov scores third Top 5 win in the last month with victory over Medvedev in Paris |url=https://www.tennis.com/news/articles/grigor-dimitrov-scores-third-top-5-win-in-the-last-month-medvedev-paris |access-date=2023-11-15 |website=Tennis.com |language=en}}</ref> and sixth top-10 of the season, tied together with Alex de Minaur.<ref>{{Cite web |title=Grigor Dimitrov Beats Daniil Medvedev In Paris {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/medvedev-dimitrov-paris-2023-wednesday |access-date=2023-11-15 |website=ATP Tour}}</ref> Next, he defeated Alexander Bublik in straight sets to reach back-to-back quarterfinals at a Masters level.<ref>{{Cite news |last= |first= |date=2023-11-02 |title=Ruud rails at Paris Masters schedule as Sinner pulls out after late-night win |language=en-GB |work=The Guardian |url=https://www.theguardian.com/sport/2023/nov/02/casper-ruud-tennis-paris-masters-schedule-jannik-sinner-pulls-out-late-night-win |access-date=2023-11-15 |issn=0261-3077}}</ref> He reached his second, consecutive Masters semifinal for the season defeating 11th seed Hubert Hurkacz for his 40th win.<ref>{{Cite web |title=Grigor Dimitrov Beats Hubert Hurkacz In Paris {{!}} ATP Tour {{!}} Tennis |url=https://www.atptour.com/en/news/hurkacz-dimitrov-paris-2023-friday |access-date=2023-11-15 |website=ATP Tour}}</ref> Next he defeated seventh seed Stefanos Tsitsipas and reached his first Masters final since 2017, where he lost to Novak Djokovic. As a result, he returned to the top 15, at world No. 14 on 6 November 2023.

===2024: Major and Masters quarterfinals career set, 40th Top 10 & 450th career wins===
Starting the season at [[2024 Brisbane International|Brisbane]],<ref>{{cite web|url=https://lastwordonsports.com/tennis/2024/01/05/atp-brisbane-semifinal-predictions-rune-safiullin/|title=ATP Brisbane Semifinal Predictions|date=5 January 2024}}</ref><ref>{{cite web|url=https://www.atptour.com/en/news/rune-duckworth-brisbane-2024-friday|title=Rune, Dimitrov seal SF spots in Brisbane|date= 5 January 2024}}</ref> he reached his third final at the tournament and 18th in his career overall defeating Andy Murray, Daniel Altmaier, wildcard [[Rinky Hijikata]] and [[Jordan Thompson (tennis)|Jordan Thompson]].<ref>{{cite web|url=https://www.atptour.com/en/news/rune-safiullin-brisbane-2024-saturday|title=Rune surges past Safiullin, sets Dimitrov final in Brisbane|date= 6 January 2024}}</ref> He defeated top seed [[Holger Rune]] in the final to win his ninth title and first since 2017.<ref>{{cite web|url=https://www.atptour.com/en/news/rune-dimitrov-brisbane-2024-final|title= His parents left early, but Dimitrov stayed to finish the job in Brisbane final}}</ref><ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-captures-first-title-2240-days-brisbane-final-win-over-holger-rune|title= Grigor Dimitrov captures first title in 2,240 days with Brisbane final win over Holger Rune}}</ref> With the title win, he recorded more match wins (23) than any other player at this tournament. As a result, he moved to No. 13 in the singles rankings on 8 January 2024, his highest since 2018.<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-pepperstone-atp-rankings-8-january-2024|title= Dimitrov climbs following Brisbane title, Mover of Week}}</ref>

Seeded 13th at the [[2024 Australian Open]] where he made his record 52nd consecutive major appearance, he reached the second round with a win over Marton Fucsovics, and then won over Kokkinakis in the second round, but lost in the third round to [[Nuno Borges (tennis)|Nuno Borges]].<ref>{{cite web |url=https://ausopen.com/articles/news/day-3-mens-wrap-rune-wrestles-ruud-redecorates |title= Day 3 men's wrap: Rune wrestles, Ruud redecorates|date=16 January 2024}}</ref><ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-is-still-working-to-make-the-most-of-his-once-legendary-potential|title=Grigor Dimitrov is still working to make the most of his once-legendary potential|date=16 January 2024}}</ref>

He reached his second final of the season in [[2024 Open 13 Provence|Marseille]] defeating [[Sebastian Korda]], [[Arthur Rinderknech]]<ref>{{cite web|url= https://www.tennis.com/news/articles/grigor-dimitrov-hurkacz-khachanov-humbert-marseille-four-wins-no-break-points|title= Grigor Dimitrov completes Top 4 domination in Marseille: four wins, no break points faced}}</ref><ref>{{cite web|url=https://www.atptour.com/en/news/hurkacz-machac-marseille-2024-friday|title= Hurkacz, Dimitrov hurry into Marseille SFs }}</ref> and Karen Khachanov.<ref>{{cite web|url=https://www.atptour.com/en/news/hurkacz-humbert-marseille-2024-sfs-saturday|title=Dimitrov wins Marseille SF thriller, sets Humbert final|date=10 February 2024}}</ref> In the final he lost to fourth seed Ugo Humbert.<ref name=Marseille>{{cite web|url=https://www.atptour.com/en/news/humbert-feature-doha-2024-tuesday|title=Not just a player & girlfriend, Andrianjafitrimo coaches boyfriend Humbert to Marseille title|date=20 February 2024}}</ref>
He reached back to back semifinals at the [[2024 ABN AMRO Open|Rotterdam Open]], defeating [[Lorenzo Sonego]], again Marton Fucsovics and [[Alexander Shevchenko (tennis)|Alexander Shevchenko]]. He lost in the semifinals to Alex de Minaur,<ref>{{cite web|url=https://www.atptour.com/en/news/de-minaur-dimitrov-rotterdam-2024-saturday|title=Birthday revenge! De Minaur downs Dimitrov, reaches Rotterdam final}}</ref> ending the week with the most ATP singles wins, at 13, since the beginning of the season.

In [[2024 BNP Paribas Open|Indian Wells]], he reached the fourth round defeating two Frenchmen [[Alexandre Müller]] and 21st seed [[Adrian Mannarino]]. As a result, he returned to his highest ranking of world No. 12 on 18 March 2024 for the first time since 29 October 2018 when he was ranked at No. 10.<ref>{{cite web|url=https://bnr.bg/en/post/101964162/grigor-dimitrov-and-viktoriya-tomova-climb-the-world-tennis-rankings|title=Grigor Dimitrov and Viktoriya Tomova climb the world tennis rankings}}</ref> Seeded 11th at the [[2024 Miami Open]], he reached the fourth round defeating [[Alejandro Tabilo]] in three sets<ref>{{cite web|url= https://www.novinite.com/articles/225054/Bulgarian+Tennis+Player+Grigor+Dimitrov+Secures+Hard-Fought+Victory+in+Miami+Tournament|title= Bulgarian Tennis Player Grigor Dimitrov Secures Hard-Fought Victory in Miami Tournament|date=25 March 2024}}</ref> and [[Yannick Hanfmann]] in a 46 minutes match, conceding one game.<ref>{{cite web|url=https://www.tennismajors.com/atp/dimitrov-in-a-hurry-beats-hanfmann-in-just-46-minutes-751812.html |title= Dimitrov in a hurry! Beats Hanfmann in just 46 minutes|date =26 March 2024 }}</ref> He won his next match against world No. 9 and eight seed [[Hubert Hurkacz]] and thus completed the full career set of quarterfinal showings at all nine active Masters events becoming the ninth active man to accomplish this feat after Nadal, Djokovic, Murray, Monfils, Čilić, Thiem, Tsitsipas and Zverev.<ref>{{cite web|url=https://www.atptour.com/en/news/alcaraz-musetti-miami-2024-tuesday |title= Showtime Alcaraz ousts Musetti; Dimitrov buries his Miami 'kryptonite' |date=27 March 2024}}</ref> With making his 19th Masters quarterfinal in Miami, he reached that stage or higher of at least one Masters event every season for 12 years in a row since 2013.<ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-battles-past-hubert-hurkacz-to-complete-career-set-of-masters-1000-quarterfinals-miami-open|title=Grigor Dimitrov battles past Hubert Hurkacz to complete career set of Masters 1000 quarterfinals|date=26 March 2024}}</ref><ref>{{cite web|url=https://www.atptour.com/-/media/a335e6382d2a43539c109bb7244584ca.pdf|title=ATP Media Notes DAY 7|date=26 March 2024}}</ref> With his 40th top 10 win over world No. 2 and top seed Carlos Alcaraz in the quarterfinals, he reached the semifinals of all Masters with the exception of the Madrid Open. He became just the third man born in 1990 or later to record 40 or more Top 10 wins after [[Alexander Zverev]] and [[Daniil Medvedev]] and the eight active player overall.<ref>{{cite web|url=https://www.atptour.com/en/news/alcaraz-dimitrov-miami-2024-qfs |title= Devastating Dimitrov downs Alcaraz in Miami|date=28 March 2024 }}</ref><ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-upsets-carlos-alcaraz-in-miami-quarterfinals-for-40th-top-10-win-of-career|title= Grigor Dimitrov upsets Carlos Alcaraz in Miami quarterfinals for 40th Top 10 win of career |date=28 March 2024}}</ref><ref>{{ cite web |url=https://www.miamiopen.com/2024/medvedev-sinner-rematch-collins-alexandrova-settle-womens-final-four-2/|title= Dimitrov stuns Alcaraz, plays Zverev in semifinal|date=28 March 2024}}</ref> Dimitrov reached his third Masters final defeating back to back top 5 players (last time was in Brisbane 2017), for his first win against fourth seed Alexander Zverev in 10 years, and 20th overall against the top 5. He returned for the first time in 260 weeks (3rd longest gap in the Open Era) since November 2018 to the top 10 at world No. 9 in the rankings.<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-zverev-miami-2024-sf|title=Dimitrov sets Sinner showdown, earns Top 10 return|date=29 March 2024}}</ref><ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-and-the-one-handed-backhand-are-back-in-the-top-10-sinner-collins-medvedev|title=Grigor Dimitrov and the one-handed backhand are back in the Top 10 of the ATP rankings|date=1 April 2024}}</ref> In the final, he lost in straight sets to world No. 3 and second seed [[Jannik Sinner]].<ref>{{Cite web |title=Jannik Sinner defeats Grigor Dimitrov in Miami final {{!}} ATP Tour {{!}} Tennis |url=http://www.atptour.com/en/news/sinner-dimitrov-miami-2024-final |access-date=2024-04-03 |website=ATP Tour |language=en}}</ref>

At the [[2024 Monte-Carlo Masters]], he played the longest best-of-three match in the tournament history lasting 3 and half hours before succumbing to seventh seed [[Holger Rune]] in the round of 16. It was also the third-longest match of any kind at this Masters 1000.<ref>{{cite web|url=https://www.atptour.com/en/news/rune-dimitrov-monte-carlo-2024-thursday|title=Rune saves 2 MPs vs. Dimitrov to complete Monte-Carlo double duty|date=11 April 2023}}</ref> At the [[2024 Italian Open (tennis)|2024 Italian Open]] he reached again the round of 16, for the first time since 2020 at this Masters, defeating two lefties [[Yoshihito Nishioka]] and qualifier [[Térence Atmane]].<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-fritz-korda-rome-2024-sunday|title=Dimitrov wins 'one of the most difficult matches of the year' to advance in Rome|date=12 May 2024}}</ref> In the fourth round, he lost to 11th seed [[Taylor Fritz]] in three sets.<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-fritz-rome-2024-tuesday|title=Fritz keeps composure to down Dimitrov in Rome|website=ATPtour com|date=14 May 2024|accessdate=17 June 2024}}</ref>

With his win in the round of 16 over Hubert Hurkacz at the [[2024 French Open]], Dimitrov became the second player born in the 1990s, after Daniil Medvedev, to complete the career set of both Grand Slam and Masters 1000 quarterfinals and the sixth active player overall to accomplish the feat (after Djokovic, Nadal, Murray, Marin Čilić and Medvedev).<ref name=CareerSetQF /><ref name="atptour.com">{{cite web|title=Dimitrov puts body on the line to down Hurkacz, reaches maiden Roland Garros QF|url=https://www.atptour.com/en/news/dimitrov-hurkacz-roland-garros-2024-sunday|date=2 June 2024|accessdate=2 June 2024|website=ATPtour.com}}</ref><ref>{{cite web|title=DIMITROV TAKES THE EXTRA STEP|url=https://www.rolandgarros.com/en-us/article/rg2024-dimitrov-takes-the-extra-step|date=3 June 2024|accessdate=3 June 2024|website=RolandGarros.com}}</ref>

At the [[2024 Wimbledon Championships]], he came back from two sets to love deficit for the second time in his career, defeating [[Shang Juncheng]] to reach the third round. It was the ninth overall comeback from two sets down in a single edition of the All England Club, tying the record (with 1974, 1990 and 1997) for most comebacks at the tournament in the [[Open Era]].<ref>{{cite web|url=https://www.atptour.com/en/news/wimbledon-2024-two-set-comebacks|title=Wimbledon history! Dimitrov ties this Open Era record...|date=4 July 2024|accessdate=4 July 2024}}</ref>

At the [[2024 US Open (tennis)|US Open]], he reached again the round of 16 for a third Grand Slam in a row in the season, with straight sets wins over qualifier [[Kyrian Jacquet]], [[Rinky Hijikata]] and [[Tallon Griekspoor]], not facing a break point in the last match.<ref>{{cite web|url=https://www.atptour.com/en/news/rublev-lehecka-dimitrov-griekspoor-us-open-2024-friday|title=Dimitrov, Rublev set R4 clash in New York|date=30 August 2024|website=ATPTour}}</ref> He defeated sixth seed [[Andrey Rublev]] in five sets, his 450th career win, to reach his second quarterfinal at this Grand Slam and eight overall. He became the first player born in the 1990s to reach 300 hardcourt wins.<ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-battles-past-andrey-rublev-at-us-open-to-reach-double-career-milestone|title=Grigor Dimitrov battles past Andrey Rublev at US Open to reach double career milestone|date=1 September 2024|website =Tennis.com}}</ref>

He was selected as part of the winning team Europe for a second time at the [[2024 Laver Cup]].<ref>{{cite web|url=https://lavercup.com/news/2024/09/16/grigor-dimitrov-an-irrepressible-force|title=Grigor Dimitrov: An Irrepressible Force|website=LaverCup|date=17 September 2024}}</ref><ref>{{cite web|url=https://lavercup.com/player/grigor-dimitrov|title=Laver Cup Grigor Dimitrov Bio}}</ref> At the [[2024 Shanghai Masters]], Dimitrov recorded his 40th win for the season defeating 20th seed [[Alexei Popyrin]], to reach the round of 16. It was his second consecutive season where he recorded 40+ wins.<ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-has-won-40-or-more-matches-in-back-to-back-years-for-the-first-time-shanghai-popyrin|title=Grigor Dimitrov has won 40 or more matches in back-to-back years for the first time in his career|date=8 October 2024|website=tennis.com}}</ref> With reaching the semifinals at the [[2024 Stockholm Open]], he recorded his 100th indoor win over [[Dominic Stricker]], becoming the first man born in the 1990 or later to accomplish the feat.<ref>{{cite web|url=https://www.tennis.com/news/articles/grigor-dimitrov-storms-to-100th-indoor-win-of-career-with-victory-over-stricker-in-stockholm|title=Grigor Dimitrov storms to 100th indoor win of career with victory over Stricker in Stockholm|date=19 October 2024|website=tennis.com}}</ref> Dimitrov reached his 21st ATP career final,  fourth of the season, and third at the tournament, defeating seventh seed [[Tallon Griekspoor]] in three sets.<ref>{{cite tweet|url=https://x.com/TennisTV/status/1847709236085555515|number=1847709236085555515|title=Grigor Fights On! 😮‍💨 @GrigorDimitrov toughs out a 2-6 7-5 6-4 win over Griekspoor to reach the Stockholm final #bnppnordicopen|date=19 October 2024|user=TennisTV}}</ref><ref>{{cite web|url=https://www.atptour.com/en/news/paul-wawrinka-dimitrov-griekspoor-stockholm-2024-sfs|title=Paul eases past Wawrinka in Stockholm SFs, boosts Turin hopes|date=19 October 2024|website=ATPTour}}</ref> At the [[2024 Rolex Paris Masters]] where he was a previous year runner-up, Dimitrov made his 20th Masters quarterfinal of his career, keeping his chances alive to qualify for the ATP Finals in Turin in November.<ref>{{cite news|url=https://www.nytimes.com/2024/10/26/sports/tennis/grigor-dimitrov-has-a-renaissance.html|title=In Tennis, Grigor Dimitrov Has a Renaissance - The New York Times|date=26 October 2024|work=[[The New York Times]]}}</ref><ref>{{cite web|url=https://www.atptour.com/en/news/medvedev-dimitrov-paris-2024-wednesday|title=Dimitrov stays alive in Turin race, Popyrin upsets Medvedev in Paris|date=30 October 2024|website=ATPTour}}</ref><ref>{{cite news|url=https://www.reuters.com/sports/tennis/alcaraz-exits-paris-masters-thriller-zverev-through-face-tsitsipas-2024-10-31/|title=Alcaraz exits Paris Masters in thriller, Zverev through to face Tsitsipas|publisher =[[Reuters]]|date=31 October 2024}}</ref><ref>{{cite web|url=https://www.tennis.com/news/articles/two-points-season-ending-grigor-dimitrov-lives-another-day-atp-finals-race-paris|title=Two points from his season ending, Grigor Dimitrov lives another day in ATP Finals race|date=31 October 2024|website=Tennis.com}}</ref> Dimitrov moved ahead of [[Roger Federer]] and tied with [[Pete Sampras]] and [[Marat Safin]] for fourth all-time record wins at the tournament with 24.<ref>{{cite web|url=https://www.thetennisgazette.com/news/grigor-dimitrov-equals-roger-federers-record-after-latest-win-at-the-paris-masters/|title=Grigor Dimitrov equals Roger Federer's record after latest win at the Paris Masters|date=30 October 2024}}</ref> He lost to Karen Khachanov in straight sets.<ref>{{cite web|url=https://www.atptour.com/en/news/khachanov-dimitrov-thompson-humbert-paris-2024-friday |title= Khachanov's hot streak sinks Dimitrov's Turin hopes in Paris|date=1 November 2023|website=ATPTour}}</ref>

===2025: 25th win in Brisbane, consecutive Miami semifinal ===
With his first round win over [[Yannick Hanfmann]] at the [[2025 Brisbane International]], Dimitrov became the player with the most wins in the tournament history, with a win-loss record of 24-6, surpassing fellow two-time titlist [[Andy Murray]].<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-hanfmann-brisbane-2025-monday |title= Dimitrov kick-starts title defence, Lehecka sinks Rune in Brisbane |date=30 December 2024|website=ATPTour}}</ref> He then defeated home favorite [[Aleksandar Vukic]] to reach the quarterfinals, his 25th record breaking win at the event.<ref>{{cite web|url=https://www.atptour.com/en/news/dimitrov-vukic-brisbane-2025-wednesday |title= A quiet New Year's Eve helps Dimitrov march on in Brisbane |date=1 January 2025|website=ATPTour}}</ref>

At the [[2025 Miami Open]] where he was defending runner-up points from 2024, Dimitrov reached the quarterfinals with wins over 22nd seed [[Karen Khachanov]] and 31st seed [[Brandon Nakashima]].<ref> {{cite web|url=https://www.atptour.com/en/news/ruud-cerundolo-de-minaur-berrettini-miami-2025-tuesday |title= Cerundolo sinks Ruud to reach Miami QFs, Dimitrov advances |date=25 March 2025}}</ref> He reached consecutive semifinals at the tournament defeating 23rd seed [[Francisco Cerúndolo]] after nearly three hours, in three sets, while saving a match point in the process.<ref> {{cite web|url=https://www.atptour.com/en/news/cerundolo-dimitrov-miami-2025-qfs|title= Dimitrov saves MP, survives Cerundolo after nearly 3 hours|date=27 March 2025}} </ref>

==National representation==
===Davis Cup===
Dimitrov made his [[Davis Cup]] debut for [[Bulgaria Davis Cup team|Bulgaria]] in 2008 as a 16-year-old. Playing in front of a home crowd in [[Plovdiv, Bulgaria|Plovdiv]], the teenage Dimitrov compiled an undefeated record in both singles and doubles to promote his country into the second division of the Europe/Africa zone. A 17-year-old Dimitrov returned to the Bulgarian Davis Cup team for the first round of the Davis Cup Europe/Africa zone in 2009. Dimitrov was victorious in both his singles rubbers which led to a narrow 3–2 victory over [[Hungary Davis Cup team|Hungary]]. He would then take a few breaks from Davis Cup which would result in Bulgaria being relegated back to the lowest division of Davis Cup.

Dimitrov would return to Davis Cup competition in 2012 as a top 100 player. The Bulgarians breezed through the round-robin tournament held in their home city of Sofia and would once again be promoted to the second division of the Europe/Africa zone. Dimitrov and the Bulgarian Davis Cup team have been unable to advance past the first round since being promoted but have been victorious in their two relegation ties.

===Olympics===
Dimitrov represented [[Bulgaria at the 2012 Summer Olympics|Bulgaria]] at his maiden Olympics in [[Tennis at the 2012 Summer Olympics|2012 London]]. He competed in the singles competition and advanced past the first round with a straight sets victory over Poland's [[Łukasz Kubot]]. He was then beaten by France's 12th seed [[Gilles Simon]]. Dimitrov made his second Olympic appearance in [[Tennis at the 2016 Summer Olympics|2016 Rio]] where he was beaten in the first round of the singles competition by Croatian [[Marin Čilić]].

Dimitrov skipped the [[Tennis at the 2020 Summer Olympics|2020 Tokyo Olympics]] and registered to play at the ATP 250 tournament in Atlanta instead but later withdrew, as he did not meet the minimal [[Tennis at the 2020 Summer Olympics – Qualification|qualifications requirements]] due to non-representation in the Davis Cup.<ref>{{cite web|url=https://www.essentiallysports.com/nick-kyrgios-atp-tennis-news-jannik-sinner-nick-kyrgios-jannik-sinner-grigor-dimitrov-to-skip-tokyo-olympics-confirmed-as-entries-at-atlanta-atp-250-2021/|title=Nick Kyrgios, Jannik Sinner, Grigor Dimitrov to Skip Tokyo Olympics, Confirmed as Entries at Atlanta ATP 250 2021|date=9 July 2021}}</ref>

==Coaching==
As a child, Dimitrov was coached by his father, Dimitar, at Tennis Club Haskovo. As his talent became more apparent he started to receive coaching from abroad, most notably from Spaniard Pato Alvarez, who has also coached Britain's [[Andy Murray]]. Alvarez has reportedly said that Dimitrov is the best 17 year old he has coached. Around the time of his success at the [[2009 ABN AMRO World Tennis Tournament – Singles|2009 Rotterdam Open]], Dimitrov formally began a coaching relationship with [[Peter Lundgren]], former coach of world No. 1s [[Marat Safin]] and [[Roger Federer]]. Lundgren has also been quick to praise Dimitrov, saying that "he is better than Federer was at his age."<ref>{{Cite web |url=http://ontennis.com/news/lundgren:-grigor-dimitrov-even-better-federer |title=Lundgren: Grigor Dimitrov is even better than Federer |date=13 February 2009 |access-date=2021-11-23 |website=ontennis.com |archive-date=19 March 2009 |archive-url=https://web.archive.org/web/20090319144524/http://ontennis.com/news/lundgren:-grigor-dimitrov-even-better-federer |url-status=dead }}</ref>

In June 2010, Dimitrov ended his coaching relationship with Lundgren and was subsequently coached by Australian pro [[Peter McNamara]].<ref>{{Cite web|title=Peter McNamara is the New Coach of Grigor Dimitrov :. Grigor Dimitrov|url=https://www.grigor-dimitrov.com/news/show/article/peter-mcnamara-is-the-new-coach-of-grigor-dimitrov|access-date=2021-11-23|website=www.grigor-dimitrov.com}}</ref> Dimitrov and McNamara have ended their coaching relationship at the end of the 2011 season. In 2012, Dimitrov was coached by [[Patrick Mouratoglou]] in an attempt to revive his fortunes.<ref>{{cite web|url=http://www.tennishead.net/on-tour/1273404/dimitrov_appoints_mouratoglou_as_coach.html|archive-url=https://archive.today/20130222060343/http://www.tennishead.net/on-tour/1273404/dimitrov_appoints_mouratoglou_as_coach.html|url-status=dead|archive-date=22 February 2013|title=Dimitrov appoints Mouratoglou as coach|date=25 March 2012|access-date=25 March 2012}}</ref> On 26 November 2012, Dimitrov left the Patrick Mouratoglou Academy and joined the [[Good to Great Tennis Academy]] in Sweden, which is run by ex-touring pros [[Magnus Norman]], [[Nicklas Kulti]], and [[Mikael Tillström]].

On 7 October 2013, Dimitrov announced on his Facebook page that he has hired [[Roger Rasheed]] (former coach of Gaël Monfils, Jo-Wilifred Tsonga and Lleyton Hewitt) to be his new coach.<ref>{{cite web|url=https://www.facebook.com/grigordimitrovtennis?hc_location=stream|title=Security Check Required|website=www.facebook.com}}</ref> On 7 July 2015 Dimitrov announced via Twitter that he would be parting ways with coach Roger Rasheed.<ref>{{cite tweet|number=618183254391156737|user=GrigorDimitrov|title=After much thought I have decided to end my working relationship with Roger.|date=6 July 2015}}</ref> On 25 September 2015, Dimitrov announced he had hired [[Juan Martín del Potro]]'s former coach [[Franco Davín]],<ref name="Davin">{{cite web | url=http://www.tennis.com/pro-game/2015/09/dimitrov-hires-former-del-potro-coach-franco-davin/56426/#.VpoXMmQrJE5 | title=Dimitrov hires Del Potro's former coach, Franco Davín | publisher=tennis.com | date=25 September 2015 | access-date=14 January 2016 | author=Cronin, Matt}}</ref> but they parted ways in the first half of 2016.<ref>{{cite web|title=DIMITROV, DAVIN NO LONGER WORKING TOGETHER; 'THINGS JUST HAVEN'T WORKED OUT'|url=http://www.tennis.com/pro-game/2016/07/dimitrov-davin-no-longer-working-together-things-just-havent-worked-out/59384/|website=www.tennis.com|access-date=1 December 2017}}</ref>

Since June 2016, Dimitrov has been coached by [[Daniel Vallverdu]], a former coach of Andy Murray, during which tenure Murray won 2 Grand Slam Titles. Dimitrov has credited Vallverdu with his upturn in form during the [[2017 ATP World Tour|2017 season]] and has mentioned several times during interviews and during his thank you speech, following his win of the [[2017 ATP Finals – Singles|2017 ATP Finals]], that he is very thankful for his success to his coaching team and particularly Vallverdu. Dimitrov also stated numerous times through the season, that Valverdu changed his mentality towards the game and is the main factor for the way he plays against top ten players.<ref>{{cite web|title=Taming The Talent: Why Dimitrov & Vallverdu Are A Winning Match|url=http://www.atpworldtour.com/en/news/vallverdu-atp-finals-2017-review-tuesday-atp|website=www.atpworldtour.com|access-date=1 December 2017}}</ref><ref>{{cite web|url=http://corner.dir.bg/news.php?id=26618018 |title=Валверду: С Григор тренираме по 8 часа на ден &#124; Корнер.dir.bg |publisher=Corner.dir.bg |date= 23 November 2017|accessdate=2021-11-23}}</ref> On 7 May 2019, Dimitrov declared that he and Vallverdu had parted ways following a string of unsuccessful tournament participations.<ref>{{cite web|title=Dimitrov Announces Split With Vallverdu|url=https://www.atptour.com/en/news/dimitrov-vallverdu-part-ways-madrid-2019|website=www.atptour.com|access-date=8 May 2019}}</ref>

Since 3 January 2021, Dimitrov was coached by Dante Bottini. Dante Bottini replaced the German coach Christian Groh, with whom Dimitrov worked during 2020.<ref>{{cite web|url= https://www.essentiallysports.com/grigor-dimitrov-announces-coaching-changes-for-australian-open-2020/|title=Dimitrov announces coaching changes for 2020|date=10 December 2019|access-date=11 December 2019}}</ref><ref>{{cite web | url=https://thetennistime.com/grigor-dimitrov-coach/ | title=Who is Grigor Dimitrov's coach in 2022? | date=12 August 2022 }}</ref> The most serious successes of the new coach are linked to Japanese Kei Nishikori, who managed to climb to number 4 in the world rankings under his guidance. He split with Bottini in September 2022.<ref>{{cite web | url=https://corner.dir.bg/tenis/grigor-dimitrov-uvolni-trenyora-si | title=Григор Димитров уволни треньора си | date=13 September 2022 }}</ref><ref>{{cite web | url=https://darik.news/en/grigor-dimitrov-broke-up-with-dante-bottini-tenniskafe.html | title=Grigor Dimitrov broke up with Dante Bottini – TennisKafe | date=13 September 2022 }}</ref>

In October 2022, after parting ways with Wawrinka, Vallverdu agreed to coach Dimitrov again till the end of the 2022 season which ended in November 2022.<ref>{{Cite web|url= https://www.tenniskafe.com/atp/grigor-dimitrov/dimitrov-shte-raboti-s-valverdu-do-kraya-na-sezona/|title=Dimitrov will work with Valverdu till the end of the 2022 season|date=18 October 2022|access-date=19 November 2022}}</ref> On 1 December 2022, it was confirmed he will work with Dimitrov also in 2023.<ref>{{cite web | url=https://www.tenniskafe.com/atp/grigor-dimitrov/dimitrov-shte-raboti-s-valverdu-i-prez-2023/ | title=Димитров ще работи с Валверду и през 2023 | date=30 November 2022 }}</ref>

==Playing style==
Dimitrov employs an all-round style of playing, and is said to have one of the most unusual play styles on the Tour. His flexibility and the fact that he's comfortable on all parts of the court is the main reason why many people said during his early years that he was one of the most talented up-and-coming players. Dimitrov is known for his hustle, athleticism, fluid style of play and exceptional shot-making.

Dimitrov employs an eastern to semi-western grip on his forehand, somewhat similar to that of [[Roger Federer]].<ref>{{cite web|url=https://www.tenniscompass.com/eastern-forehand-grip-guide.html|title= Eastern Forehand Grip in Tennis}}</ref> His forehand is known to be very heavy, powerful and accurate and is his primary weapon. He uses it to generate sudden pace in baseline rallies, often catching his opponents off guard. Dimitrov employs a conventional [[single-handed backhand]]. His backhand is one of the most versatile in the game<ref>{{cite web|author=Mohab Ghobranios |url=https://www.yahoo.com/gma/view-baseline-top-5-one-handed-backhands-atp-tour-084303927.html |title=View from the Baseline: Federer, Wawrinka and the top one-handed backhand players on the ATP Tour |publisher=Yahoo.com |date=2017-04-12 |accessdate=2021-11-23}}</ref><ref>{{cite web|first=Mohab |last=Ghobranios |url=https://au.sports.yahoo.com/best-backhand-atp-tour-roger-federer-stan-wawrinka-35059848.html |title=Who has the best backhand on the ATP tour? |publisher=Au.sports.yahoo.com |date=2017-04-16 |accessdate=2021-11-23}}</ref> due to his ability to hit it with top-spin, flat, and his backhand slice, which [[John McEnroe]] has said is the best slice in the game. He also has a slightly unusual follow-through and finish on his backhand, often straightening out his hand and extending it all the way across his waist, which some have said is a weakness due to the time taken to recover by recoiling his arm. Dimitrov usually uses his backhand as a rally stroke to build up points rather than hit immediate winners, although he is known to be able to generate significant pace on his backhand when returning a weak shot from his opponent or when neutralising a fast-paced shot. He has displayed this ability more than 50 times alone in his semi-final against Rafael Nadal on the Australian Open 2017.

Dimitrov has a solid fast serve, often reaching 210&nbsp;km/h, (130&nbsp;mph) up to {{convert|220|km/h|mph|abbr=on}}. His first serve has been known to be pivotal, often producing aces on important points. Dimitrov employs more top-spin on his second serve, making it slower but more consistent. In 2017 however he had a big problem with double faults as he made 254 of them (around 40 more than 2016), although he made his best season so far.

One aspect of Dimitrov's game that has been widely praised is his variety and flexibility. He is comfortable playing on all areas of the court, having solid ground strokes and exceptional touch at the net. He also employs aggressive drop shots to catch opponents off guard and is even known to frequently use fakes, especially on the forehand side, to fake drop shots instead of fast ground strokes, wrongfooting opponents. His speed and athleticism are also exceptional, as is famous for using slide, sometimes even to the point of splitting, to reach balls. He also occasionally dives to reach balls, one of the most famous occasions being his second round match at the [[Monte-Carlo Masters]] against [[Janko Tipsarević]], in which he dove to hit a drop-shot, winning him the point. His all-round play has had many commentators and past players call him "classy" and "stylish".

Dimitrov is also noted as one of the only players on the tour who can consistently produce trick shots, alongside [[Gaël Monfils]], [[Dustin Brown (tennis)|Dustin Brown]], [[Nick Kyrgios]] and Roger Federer. He has been known to hit a variety of trick shots and unorthodox shots, such as the [[Tweener (tennis)|tweener]]. Sometimes, he does it for entertainment purposes, eventually losing the point. Some of his most famous trick shots include his behind the back drop-shot against [[Viktor Troicki]] in the [[Swiss Indoors]] 2012 and his successive between-the-leg shots off [[Jack Sock]]'s returns in the [[Stockholm Open]] 2014. Both shots were considered among the best trick shots ever, with the former considered the shot of the year in 2012.

Early in his career, Dimitrov was compared to Roger Federer due to their similarity in play style and actions, notably his forehand, backhand and serve, earning him the nickname "Baby Fed". Over the years he has attempted to shed this title and has had people appreciate his own style.<ref>{{Cite web |date=2022-04-18 |title='He Was Not That Well Known'- Grigor Dimitrov Explains How He Ended Up Having Roger Federer's Game Style |url=https://www.essentiallysports.com/atp-tennis-news-he-was-not-that-well-known-grigor-dimitrov-explains-how-he-ended-up-having-roger-federers-game-style/ |access-date=2023-11-15 |website=EssentiallySports}}</ref> Dimitrov has won one of his eight meetings with Federer, at the US Open 2019.

==Equipment==
As of 2013, Dimitrov uses a customized [[Wilson Sporting Goods|Wilson]] mid-size 93 square inches prototype racket provided by the Wilson Pro Room Team (as disclosed by pro tour stringers such as the Priority One team members), cosmetic on it is the Pro Staff 95 BLX, it is weighted about 12.oz strung with a 16X19 string pattern. In 2014, he switched to 18X17 string pattern. From 2015 and on, he switched to a 97 square inches head size, similar to Federer's frame but with a 18X17 pattern. In 2016, he worked with Wilson Pro Room Team to come up with the model now known as the Pro Staff 97S with a thinner beam width of 19.5mm. From the start of his adult career in 2010, he was sponsored by [[Nike, Inc.|Nike]] wearing the brand apparel and the Nike Air Zoom Vapor Pro, he previously wore the Air Zoom Vapor X which was also Federer's shoe of choice until 2021. From the [[2023 French Open]] onwards, Dimitrov became an ambassador for [[Lacoste]].

==Endorsement and Sponsorships==
Dimitrov’s professional endorsement agreements include [[Nike, Inc.|Nike]],<ref name="sponsors"/> [[Wilson Sporting Goods]]<ref>{{cite web |title=Grigor Dimitrov |url=https://www.wilson.com/en-us/explore/tennis/grigor-dimitrov |website=Wilson Sporting Goods |access-date=8 February 2024 |archive-date=23 January 2023 |archive-url=https://web.archive.org/web/20230123170508/https://www.wilson.com/en-us/explore/tennis/grigor-dimitrov |url-status=dead }}</ref> and in 2023 concluded a deal with [[Lacoste|Lacoste Apparel Products and Lacoste Accessories]].<ref>{{cite web |title=Grigor Dimitrov – The New Lacoste Ambassador |url=https://www.lacoste.com/gb/news/sports/grigor-dimitrov-new-ambassador-2023.html |website=Lacoste |access-date=8 February 2024|date=30 May 2023}}</ref> Historically he has acted as a brand ambassador to [[Rolex]],<ref name=sponsors>{{cite web |last1=Saha |first1=Rahul |title=Grigor Dimitrov's Sponsors and Brand endorsements |url=https://sportskhabri.com/grigor-dimitrovs-sponsors-list/ |website=Sports Khabri |access-date=8 February 2024}}</ref> [[Häagen-Dazs|Haagen Dazs]],<ref name=sponsors /> [[American Express]],<ref>{{cite web |last1=Bristol |first1=Georgi |title=Григор Димитров се включи в реклама на American Express |url=https://tennis.bg/article/grigor-dimitrov-se-vkljuchi-v-reklama-i-na-american-express-video/11637/ |website=Tennis |date=22 October 2018 |access-date=8 February 2024}}</ref> [[JetSmarter|Jet Smarter]],<ref>{{cite web |title=Григор Димитрова стана лице на чартърна компания |url=https://www.sportlive.bg/timeout/facefromnews/Grigor-Dimitrov-stana-reklamno-lice-na-chartyrna-kompaniq-665966.html |website=Sport Live |date=22 March 2018 |access-date=8 February 2024}}</ref> Vitamin Well,<ref>{{cite web |title=Q&A WITH GRIGOR DIMITROV |url=https://www.vitaminwell.com/qa-with-grigor-dimitrov/ |website=Vitaminwell |date=24 July 2019 |access-date=8 February 2024}}</ref> Creed<ref>{{cite web |title=Viking Diaries: Grigor Dimitrov |url=https://creedboutique.com/blogs/creed-journal/viking-diaries-grigor-dimitrov |website=Creed |access-date=8 February 2024}}</ref> and [[Telenor]]<ref>{{cite web |title=Site Media |url=https://sitemedia.bg/en/news/telenor-extends-its-partnership-grigor-dimitrov-and-launches-prize-campaign-his-fans |website=Telenor extends its partnership with Grigor Dimitrov and launches a prize campaign for his fans |date=23 January 2017 |access-date=8 February 2024}}</ref> and in 2023 entered into multilevel partnership agreement with [[Bianchet]].<ref>{{cite web |title=Friends and Partners |url=https://www.bianchet.com/partners-friends|website=Bianchet |access-date=8 February 2024}}</ref>

==Honours and awards==
Best young tennis player in Bulgaria – 2005<ref name=bgtennis22.bg>{{cite web | title =Годишни награди на Българска Федерация по Тенис – 2005 | work =bgtennis.bg | date =2005 | url =http://bgtennis.bg/pub/docs/nagradi.pdf | access-date =2015-03-16 | archive-url =https://web.archive.org/web/20150402095937/http://bgtennis.bg/pub/docs/nagradi.pdf | archive-date =2 April 2015 | url-status =dead }}</ref>

[[Bulgarian Sportsperson of the Year]] – 2014,<ref name="topsport100005"/> 2017<ref name=topsport2017>
{{cite web | title=Григор Димитров е най-добрият спортист на България за 2017–а година! |url=https://topsport.bg/sport/grigor-dimitrov-e-nay-dobriyat-sportist-na-balgariya-za-2017-a-godina.html|date=2017}}</ref>

Sports Icarus Award — 2014,<ref>{{Cite web|url=https://bnr.bg/en/post/100500064/grigor-dimitrov-receives-sports-icarus-award|title=Grigor Dimitrov receives Sports Icarus Award|website=bnr.bg|accessdate=26 June 2023}}</ref> 2017<ref name="topsport2017"/><ref>{{Cite web|title=Big Sports Icarus for Achievement of the Year goes to Grigor Dimitrov|url=https://bnr.bg/en/post/100908364/big-sports-icarus-for-achievement-of-the-year-goes-to-grigor-dimitrov|access-date=2021-11-23|website=bnr.bg}}</ref>

[[Balkan Athlete of the Year]] — 2017<ref name="reuters1" /><ref name="topsport2017"/><ref name="autogenerated1"/>

* '''Won''' – [[ATP Awards|ATP Stefan Edberg Sportsmanship Award]] (2024)

==Career statistics==
{{Main|Grigor Dimitrov career statistics}}

===Grand Slam tournament performance timeline===
{{Performance key|short=yes}}
''Current through the [[2025 French Open – Men's singles|2025 French Open]].''
{|class="wikitable nowrap" style=text-align:center;font-size:96%
|-
! Tournament !![[2009 ATP World Tour|2009]]!![[2010 ATP World Tour|2010]]!![[2011 ATP World Tour|2011]]!![[2012 ATP World Tour|2012]]!![[2013 ATP World Tour|2013]]!![[2014 ATP World Tour|2014]]!![[2015 ATP World Tour|2015]]!![[2016 ATP World Tour|2016]]!![[2017 ATP World Tour|2017]]!![[2018 ATP World Tour|2018]]!![[2019 ATP Tour|2019]]!![[2020 ATP Tour|2020]]!![[2021 ATP Tour|2021]]!![[2022 ATP Tour|2022]]!![[2023 ATP Tour|2023]]!![[2024 ATP Tour|2024]]!![[2025 ATP Tour|2025]]!!SR!!W–L!!Win%
|-
|  style="background:#efefef; text-align:left;"|[[Australian Open]]
|A
|[[2010 Australian Open – Men's singles qualifying|Q1]]
|bgcolor=afeeee|[[2011 Australian Open – Men's singles|2R]]
|bgcolor=afeeee|[[2012 Australian Open – Men's singles|2R]]
|bgcolor=afeeee|[[2013 Australian Open – Men's singles|1R]]
|bgcolor=ffebcd|[[2014 Australian Open – Men's singles|QF]]
|bgcolor=afeeee|[[2015 Australian Open – Men's singles|4R]]
|bgcolor=afeeee|[[2016 Australian Open – Men's singles|3R]]
| style="background:yellow;"|[[2017 Australian Open – Men's singles|SF]]
|bgcolor=ffebcd|[[2018 Australian Open – Men's singles|QF]]
|bgcolor=afeeee|[[2019 Australian Open – Men's singles|4R]]
|bgcolor=afeeee|[[2020 Australian Open – Men's singles|2R]]
|bgcolor=ffebcd|[[2021 Australian Open – Men's singles|QF]]
|bgcolor=afeeee|[[2022 Australian Open – Men's singles|2R]]
|bgcolor=afeeee|[[2023 Australian Open – Men's singles|3R]]
|bgcolor=afeeee|[[2024 Australian Open – Men's singles|3R]]
|bgcolor=afeeee|[[2025 Australian Open – Men's singles|1R]]
| bgcolor="efefef" |0 / 15
|bgcolor=efefef|33–15
|bgcolor=efefef|{{tennis win percentage|won=33|lost=15|integer=yes}}
|-
|  style="background:#efefef; text-align:left;"|[[French Open]]
|A
|A
|bgcolor=afeeee|[[2011 French Open – Men's singles|1R]]
|bgcolor=afeeee|[[2012 French Open – Men's singles|2R]]
|bgcolor=afeeee|[[2013 French Open – Men's singles|3R]]
|bgcolor=afeeee|[[2014 French Open – Men's singles|1R]]
|bgcolor=afeeee|[[2015 French Open – Men's singles|1R]]
|bgcolor=afeeee|[[2016 French Open – Men's singles|1R]]
|bgcolor=afeeee|[[2017 French Open – Men's singles|3R]]
|bgcolor=afeeee|[[2018 French Open – Men's singles|3R]]
|bgcolor=afeeee|[[2019 French Open – Men's singles|3R]]
|bgcolor=afeeee|[[2020 French Open – Men's singles|4R]]
|bgcolor=afeeee|[[2021 French Open – Men's singles|1R]]
|bgcolor=afeeee|[[2022 French Open – Men's singles|3R]]
|bgcolor=afeeee|[[2023 French Open – Men's singles|4R]]
|bgcolor=ffebcd|[[2024 French Open – Men's singles|QF]]
|bgcolor=afeeee|[[2025 French Open – Men's singles|1R]]
| bgcolor="efefef" |0 / 15
|bgcolor=efefef|21–15
|bgcolor=efefef|{{tennis win percentage|won=21|lost=15|integer=yes}}
|-
|  style="background:#efefef; text-align:left;"|[[Wimbledon Championships|Wimbledon]]
|bgcolor=afeeee|[[2009 Wimbledon Championships – Men's singles|1R]]
|A
|bgcolor=afeeee|[[2011 Wimbledon Championships – Men's singles|2R]]
|bgcolor=afeeee|[[2012 Wimbledon Championships – Men's singles|2R]]
|bgcolor=afeeee|[[2013 Wimbledon Championships – Men's singles|2R]]
|bgcolor=yellow|[[2014 Wimbledon Championships – Men's singles|SF]]
|bgcolor=afeeee|[[2015 Wimbledon Championships – Men's singles|3R]]
|bgcolor=afeeee|[[2016 Wimbledon Championships – Men's singles|3R]]
|bgcolor=afeeee|[[2017 Wimbledon Championships – Men's singles|4R]]
|bgcolor=afeeee|[[2018 Wimbledon Championships – Men's singles|1R]]
|bgcolor=afeeee|[[2019 Wimbledon Championships – Men's singles|1R]]
| style="color:dimGrey;"|NH
|bgcolor=afeeee|[[2021 Wimbledon Championships – Men's singles|2R]]
|bgcolor=afeeee|[[2022 Wimbledon Championships – Men's singles|1R]]
|bgcolor=afeeee|[[2023 Wimbledon Championships – Men's singles|4R]]
|bgcolor=afeeee|[[2024 Wimbledon Championships – Men's singles|4R]]
|
| bgcolor="efefef" |0 / 14
|bgcolor=efefef|22–14
|bgcolor=efefef|{{tennis win percentage|won=22|lost=14|integer=yes}}
|-
|  style="background:#efefef; text-align:left;"| [[US Open (tennis)|US Open]]
|[[2009 US Open – Men's singles qualifying|Q2]]
|A
|bgcolor=afeeee|[[2011 US Open – Men's singles|1R]]
|bgcolor=afeeee|[[2012 US Open – Men's singles|1R]]
|bgcolor=afeeee|[[2013 US Open – Men's singles|1R]]
|bgcolor=afeeee|[[2014 US Open – Men's singles|4R]]
|bgcolor=afeeee|[[2015 US Open – Men's singles|2R]]
|bgcolor=afeeee|[[2016 US Open – Men's singles|4R]]
|bgcolor=afeeee|[[2017 US Open – Men's singles|2R]]
|bgcolor=afeeee|[[2018 US Open – Men's singles|1R]]
|bgcolor=yellow|[[2019 US Open – Men's singles|SF]]
|bgcolor=afeeee|[[2020 US Open – Men's singles|2R]]
|bgcolor=afeeee|[[2021 US Open – Men's singles|2R]]
|bgcolor=afeeee|[[2022 US Open – Men's singles|2R]]
|bgcolor=afeeee|[[2023 US Open – Men's singles|3R]]
|bgcolor=ffebcd|[[2024 US Open – Men's singles|QF]]
|
| bgcolor="efefef" |0 / 14
|bgcolor=efefef|21–14
|bgcolor=efefef|{{tennis win percentage|won=21|lost=14|integer=yes}}
|- style="font-weight:bold; background:#efefef;"
|style=text-align:left|Win–loss
|0–1
|0–0
|2–4
|3–4
|3–4
|12–4
|6–4
|7–4
|11–4
|6–4
|9–4
|5–3
|6–4
|4–4
|10–4
|13–4
|0–2
|0 / 58
|97–58
|{{tennis win percentage|won=97|lost=58|integer=yes}}
|}

=== Year–end championship finals ===
====Singles: 1 (1 title)====
{|class="wikitable"
|-
!Result
!Year
!width=200|Tournament
!Surface
!width=200|Opponent
!width="180" class="unsortable"|Score
|- style="background:#ffc;"
|style="background:#98fb98;"|Win||[[2017 ATP Finals – Singles|2017]]||[[ATP Finals]], London||Hard (i)||{{flagicon|BEL}} [[David Goffin]]||7–5, 4–6, 6–3
|}

===Masters 1000 tournaments===
====Singles: 3 (1 title, 2 runners-up)====
{|class="sortable wikitable"
|-
!Result
!Year
!Tournament
!Surface
!width=150|Opponent
!width=125 class=unsortable|Score
|-bgcolor=ccccff
|bgcolor=98fb98|Win
|[[2017 Western & Southern Open – Men's singles|2017]]
|[[Cincinnati Open]], United States
|Hard
|{{flagicon|AUS}} [[Nick Kyrgios]]
|6–3, 7–5
|-bgcolor=ccccff
|bgcolor=ffa07a|Loss
|[[2023 Rolex Paris Masters – Singles|2023]]
|[[Paris Masters]], France
|Hard (i)
|{{flagicon|SRB}} [[Novak Djokovic]]
|4–6, 3–6
|-bgcolor=ccccff
|bgcolor=ffa07a|Loss
|[[2024 Miami Open – Men's singles|2024]]
|[[Miami Open (tennis)|Miami Open]], United States
|Hard
|{{flagicon|ITA}} [[Jannik Sinner]]
|3–6, 1–6
|}

==Records==
=== Open Era records ===
{|class="wikitable"
|-
!Time span
!Record accomplished
!Players matched
|-
|2017||Won the [[ATP Finals]] title on debut||6 others: [[Stan Smith]], [[Ilie Nastase]], [[Guillermo Vilas]], [[John McEnroe]], [[Alex Corretja]], [[Stefanos Tsitsipas]]<ref>{{Cite web|url=https://www.tennismajors.com/atp/debutants-at-the-atp-finals-the-magnificent-7-who-claimed-the-title-305244.html|title=Debutants at the ATP Finals – the magnificent 7 who claimed the title|date=14 November 2020|website=Tennis Majors|accessdate=26 June 2023}}</ref>
|-
|2011–2025||[[All-time tennis records – Men's singles#Grand Slam tournaments consecutive streaks|Longest active streak of Grand Slam appearances (58)]]||'''Stands alone'''<ref>{{Cite web|url=https://www.atptour.com/en/news/roland-garros-2022-tuesday-qualifying|title=Feliciano Lopez Falls In Roland Garros Qualifying As Grand Slam Streak Ends &#124; ATP Tour &#124; Tennis|website=ATP Tour|accessdate=26 June 2023}}</ref>
|-
|2013–2024||Active player to complete the career set of both Grand Slams and Masters quarterfinals||4 others: [[Novak Djokovic]], [[Marin Čilić]], [[Daniil Medvedev]],<ref>{{cite web |last=Berkok |first=John |date=2 June 2024 |title=Grigor Dimitrov completes career set of Grand Slam quarterfinals at Roland Garros |url=https://www.tennis.com/news/articles/grigor-dimitrov-completes-career-set-of-grand-slam-quarterfinals-at-roland-garros |accessdate=2 June 2024 |website=Tennis.com}}</ref><ref name="atptour.com"/> [[Andrey Rublev]]<ref>{{cite web|url=https://www.tennis.com/news/articles/andrey-rublev-completes-career-set-of-masters-1000-quarterfinals-in-canada|title=Andrey Rublev completes career set of Masters 1000 quarterfinals in Canada|accessdate=10 August 2024|date=10 August 2024}}</ref>

|-
|2024&ndash;2025||Male player to lose singles matches via retirement at four consecutive Grand Slams||'''Stands alone'''<ref>https://www.tennis365.com/facts-stats/grigor-dimitrov-unwanted-record-french-open-retirement-grand-slam-woes</ref><ref>https://tennistonic.com/tennis-news/868160/dimitrov-is-the-1st-player-in-the-open-era-to-lose-mens-singles-matches-via-retirement-at-4-consecutive-slams/amp/</ref>
|}

==References==
{{Reflist|30em}}

==External links==
{{Commons category|Grigor Dimitrov}}
{{Portal |Tennis}}
* {{Official website}}
* {{sports links}}
* {{ESPN Tennis}}
* {{Olympedia}}
* {{Olympics.com|grigor-dimitrov}}

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{{DEFAULTSORT:Dimitrov, Grigor}}
[[Category:1991 births]]
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