View source for Scottish Challenge Cup

{{short description|Association football competition in Scotland}}
{{distinguish|text=the [[Scottish Cup]], or the [[Scottish League Cup]]}}
{{Good article}}
{{Use dmy dates|date=September 2022}}
{{Infobox football tournament
| name                 = Scottish Challenge Cup
| logo                 =
| caption              = 
| founded              = [[1990–91 in Scottish football|1990]]
| abolished            = 
| number of teams      = 52 ([[2024–25 Scottish Challenge Cup|2024–25]])
| current champions    = [[Livingston F.C.|Livingston]] (2 titles)
| most successful club = [[Falkirk F.C.|Falkirk]] (4 titles)
| broadcasters         = [[BBC Alba]]<br />[[Premier Sports]]
| current              = [[2024–25 Scottish Challenge Cup]]
}}
The '''Scottish Professional Football League Challenge Cup''',<ref name="SFL_Final_Results">[http://www.scottishfootballleague.com/stats/records/challenge-cup/ The Scottish Football League Challenge Cup Final Results], ''scottishfootballleague.com''. [[Scottish Football League]]. Retrieved 5 April 2013.</ref><ref name="DAFC_preview">[http://www.dafc.co.uk/articles/20120725/preview-forfar-athletic_2207955_2857331 Preview Forfar Athletic] {{Webarchive|url=https://web.archive.org/web/20131101230335/http://www.dafc.co.uk/articles/20120725/preview-forfar-athletic_2207955_2857331 |date=1 November 2013 }}, ''dafc.co.uk''. [[Dunfermline Athletic F.C.]] 25 July 2012. Retrieved 5 April 2013.</ref><ref name="SFHA_Challenge_Cup">[http://scottish-football-historical-archive.com/challengecup.htm Scottish Football League Challenge Cup], ''scottish-football-historical-archive.com''. Scottish Football Historical Archive. Retrieved 5 April 2013.</ref> commonly known as the '''Scottish League Challenge Cup'''<ref name="Fisher_Sunday_Herald_Bells">Fisher, Stewart. "Beginner's Guide to the Bell's Cup ...". ''[[The Sunday Herald]]''. 4 August 2002.</ref><ref name="DUFC_LCC">[http://www.dundeeunitedfc.co.uk/index.asp?pg=292 League Challenge Cup], ''dundeeunitedfc.co.uk''. [[Dundee United F.C.]] Retrieved 5 April 2013.</ref> or '''Scottish Challenge Cup''',<ref name="SFL_Final_Results" /><ref name="DAFC_preview" /> and currently known as the '''SPFL Trust Trophy''' for sponsorship reasons, is an [[association football]] knock-out cup competition run by the [[Scottish Professional Football League]] (SPFL). It is recognised as the third most prestigious knockout trophy in Scottish football, after the [[Scottish Cup]] and the [[Scottish League Cup]].

The competition was first held during the [[1990–91 in Scottish football|1990–91 season]] as the '''[[B&Q]] Centenary Cup'''<ref name="SFL_Final_Results" /> to celebrate the 100th anniversary of the formation of the [[Scottish Football League]] (SFL). It was intended to be a one-off competition but was continued due to its popularity. It was originally contested by SFL (SPFL since 2013) teams below the top level of the [[Scottish football league system]]; select teams from lower levels of the league system were added in [[2011–12 Scottish Challenge Cup|2011–12]], and guest teams from outside Scotland in [[2016–17 Scottish Challenge Cup|2016–17]]. For the [[2019–20 Scottish Challenge Cup|2019–20]] edition there were 58 teams: 30 from the SPFL; the twelve Under-21 teams of the [[Scottish Premiership]] clubs; four each from the [[Highland Football League|Highland League]] and [[Lowland Football League|Lowland League]]; and two guest teams from each of the [[NIFL Premiership]], [[Cymru Premier]], English [[National League (English football)|National League]], and [[League of Ireland Premier Division]] up until the 2019–20 season.<ref name="SPFL Format">{{cite news|title=Scottish Challenge Cup: Bray Wanderers and Sligo Wanderers 'relishing' trophy chance|url=https://www.bbc.co.uk/sport/football/40185346|access-date=7 June 2017|publisher=BBC Sport|date=7 June 2017}}</ref>

The first winner of the tournament was [[Dundee F.C.|Dundee]], who defeated [[Ayr United F.C.|Ayr United]].<ref name="Soccer_Mistral_Challenge_Cup">[http://www.soccer.mistral.co.uk/sfleg/slcc.htm Scottish League Challenge Cup], ''soccer.mistral.co.uk''. 14 May 2001. Retrieved 5 April 2013.</ref><ref name="Sunday_Times_Centenary_Cup" /> [[Falkirk F.C.|Falkirk]] are the most successful team in the tournament with four wins, most recently in [[2012 Scottish Challenge Cup Final|2012]]. The current holders are [[Livingston F.C.|Livingston]], who defeated [[Queen's Park F.C.|Queen's Park]] in the 2025 final.<ref>{{Cite news |url=https://www.bbc.co.uk/sport/football/live/cz03vzdrgmpt |title=Queen's Park 0&ndash;5 Livingston |access-date=31 March 2025 |work=BBC Sport |language=en-GB}}</ref>

== Format ==
<!--Format for the 2016–17 competition-->The Challenge Cup is a [[single-elimination tournament|knock-out tournament]]. Within a regionalised format, clubs are paired at random and the first club drawn listed as the [[home (sports)|home team]].<ref name="SFL_Format" /> The winner of each match progresses to the next round and the loser is eliminated from the tournament. Every match, including the final, is a one-legged tie that lasts 90 minutes plus any additional [[stoppage time]]. If no clear winner has been determined after 90 minutes of normal time, 30 minutes of [[extra time]] is played. If the score is still level after extra time then the winner is decided by a [[penalty shoot-out (association football)|penalty shoot-out]].<ref name="SFL_Format" />

Beginning with the [[2016–17 Scottish Challenge Cup|2016–17 season]], the competition has been expanded to 58 entrants. All [[Scottish Professional Football League]] (SPFL) clubs will participate, with the thirty clubs from the [[Scottish Championship|Championship]], [[Scottish League One|League One]] and [[Scottish League Two|League Two]] now joined by [[SPFL Development League|Under-20 teams]] from the twelve [[Scottish Premiership|Premiership]] clubs. Also participating by invitation will be four teams each from the [[Highland Football League|Highland]] and [[Lowland Football League|Lowland Leagues]] and eight entrants from outside Scottish football – two each from the [[NIFL Premiership]] in Northern Ireland, the [[National League (English football)|National League]] in England, [[League of Ireland]] and the [[Welsh Premier League]] in Wales, until 2021 when the decision was made to only have the Scottish clubs participating due to the ongoing coronavirus pandemic. Teams are seeded to enter the competition over any of the first four rounds, after which eight teams will remain to contest the quarter-finals. The final is played at a neutral venue.<ref>{{cite news|title=Challenge Cup expansion announced – Scottish Professional Football League|url=http://spfl.co.uk/news/article/spfl-announces-challenge-cup-expansion/|access-date=9 June 2016|publisher=Scottish Professional Football League|date=8 June 2016|archive-date=7 November 2017|archive-url=https://web.archive.org/web/20171107112345/https://spfl.co.uk/news/article/spfl-announces-challenge-cup-expansion/|url-status=dead}}</ref>

In May 2024, it was announced the Cup would return to being Scottish-only for the 2024-25 season, with more Highland and Lowland League teams taking the place of the invited Northern Irish and Welsh clubs.<ref>{{cite web | url=https://www.bbc.co.uk/sport/football/articles/c044zzemkyvo | title=Prize money boost for SPFL Trust trophy as cross-border teams drop out }}</ref>

In May 2025, it was announced that for the 2025–26 edition, the cup would be reformatted to involve a 'League Phase', similar to that introduced in UEFA club competitions.<ref>{{Cite web |title=KDM Evolution Trophy 2025/26 {{!}} SPFL |url=https://spfl.co.uk/pages/challenge-cup-format |access-date=2025-06-12 |website=spfl.co.uk}}</ref> This brought around some controversy as the Premiership 'B' Teams were still in the competition at the expense of Highland and Lowland League representatives.<ref>{{Cite web |title=New Cooperation System and Challenge Cup format approved to accelerate elite player development in Scottish football |url=https://www.scottishfa.co.uk/news/new-cooperation-system-and-challenge-cup-format-approved-to-accelerate-elite-player-development-in-scottish-football/ |access-date=2025-06-12 |website=www.scottishfa.co.uk}}</ref>

== History ==
The competition was created in the [[1990–91 in Scottish football|1990–91 season]] to celebrate the 100th anniversary of the formation of the [[Scottish Football League]] in [[1890–91 in Scottish football|1890]].<ref name="SFHA_Challenge_Cup" /><ref name="Evening_Times_2007">"With the Scottish Football Museum at Hampden; Now You Know". ''[[Evening Times]]'', Glasgow. 22 December 2007.</ref> It was intended to run for only one season but continued due to its popularity. This was reflected in high attendances at matches in the later rounds of the tournament including a full capacity crowd of 11,500 at [[Fir Park]] in the first final.<ref name="DAFC_preview" /><ref name="DUFC_LCC" /><ref name="Sunday_Times_Centenary_Cup">[https://web.archive.org/web/20140407094741/http://www.thesundaytimes.co.uk/sto/sport/article200740.ece Caught in Time: Dundee win the B&Q Centenary Cup, 1990], ''thesundaytimes.co.uk''. ''[[The Sunday Times]]''. 30 April 2006. Retrieved 5 April 2013.</ref> The cup was sponsored by [[DIY]] retail company [[B&Q]] and named the ''B&Q Centenary Cup''<ref name="Daily_Record_2009_Final">[http://www.dailyrecord.co.uk/sport/football/alba-cup-final-inverness-caledonian-1042896 Alba Cup Final: Inverness Caledonian Thistle 2 Dundee 3], ''dailyrecord.co.uk''. ''[[Daily Record (Scotland)|Daily Record]]''. 23 November 2009. Retrieved 5 April 2013.</ref> for the first year and continued as the ''B&Q Cup'' for four seasons afterwards. The competition was run for three seasons without a sponsor due to the league covering the tournament costs and prize money, but was unsustainable and resulted in it being cancelled for one season in 1998–99 before being re-established in [[1999–2000 Scottish Challenge Cup|1999]] with a new sponsor.<ref name="DUFC_LCC" /> Although it is not as popular as competitions like the [[Scottish Cup]], it provides smaller clubs with a realistic opportunity of winning a trophy due to the absence of top-tier clubs from the tournament.<ref name="Fisher_Sunday_Herald_Bells" /><ref name="Times_McCarra">McCarra, Kevin. "Shootout victory for Stenhousemuir after 111 years", ''[[The Times]]'', 6 November 1995. Retrieved 23 April 2013.</ref> When [[Stenhousemuir F.C.|Stenhousemuir]] won the final in 1995 it was regarded as the club's greatest achievement in its 111-year history.<ref name="Stenhousemuir_History">[http://www.stenhousemuirfc.com/club/history/ A Brief History of Stenhousemuir Football Club], ''stenhousemuirfc.com''. [[Stenhousemuir F.C.]] Retrieved 23 April 2013.</ref> Attendances at matches in the earlier rounds of the tournament are not dissimilar to average home attendances in league competition<ref name="BBC_Rangers_opponents">{{cite web |url=https://www.bbc.co.uk/sport/0/football/18735027 |title=Rangers: Life in Scottish Division Three beckons |publisher=[[BBC Sport]] |date=14 July 2012 |access-date=23 April 2013}}</ref><ref name="Annan_v_Livingston_Round_1">{{cite web |url=http://www1.skysports.com/football/live/match/264564/form |title=Annan v Livingston – 28th Jul 2012 |publisher=[[Sky Sports]] |date=28 July 2012 |access-date=23 April 2013}}</ref> but as the competition reaches the latter stages they generally increase; [[Annan Athletic F.C.|Annan Athletic]]'s record attendance of 1,575 was set in a semi-final match against [[Falkirk F.C.|Falkirk]] in 2011.<ref name="Annan_Attendance">[http://www.annanathleticfc.com/matchdetails.asp?mid=518 "Annan Athletic 0 – 3 Falkirk"] {{webarchive|url=https://web.archive.org/web/20111004145938/http://www.annanathleticfc.com/matchdetails.asp?mid=518 |date=4 October 2011 }}, ''[[Annan Athletic F.C.]]''. 9 October 2011. Retrieved 23 April 2013.</ref><ref name="Record_attendance">[http://www.scottishfootballleague.com/news/article/record-day-at-annan/ "Record day at Annan"], ''[[Scottish Football League]]''. 12 October 2011. Retrieved 23 April 2013.</ref>

The number of competitors has varied in relation to the number of clubs with Scottish Football League membership. The first tournament featured the 28 clubs in the [[Scottish Football League First Division|First]] and [[Scottish Football League Second Division|Second Divisions]] which reduced to 26 until 1994 when the league was expanded and restructured into three divisions; increasing the number of eligible clubs to 30. In the 2010–11 competition the two highest ranked clubs from the [[Highland Football League]] with a Scottish Football Association licence were invited to compete, in order to bring the number of competitors to 32.<ref name="Highland_clubs_enter">{{cite web |url=http://news.bbc.co.uk/sport1/hi/football/13671944.stm |title=Highland duo enter new Ramsdens Cup |publisher=[[BBC Sport]] |date=6 June 2011 |access-date=6 June 2011}}</ref><ref name="Journal_Wick_Academy">[http://www.johnogroat-journal.co.uk/News/Wick-Academy-to-play-Raith-Rovers-in-Ramsdens-cup.htm Wick Academy to play Raith Rovers in Ramsdens cup], ''johnogroat-journal.co.uk''. ''[[North of Scotland Newspapers|John O'Groat Journal]]''. 12 June 2012. Retrieved 23 April 2013.</ref> Before the change in 2010, several clubs received a random [[bye (sports)|bye]] in the first round in order to even out the number of fixtures.<ref name="SFL_Format" /> The Challenge Cup continued under the auspices of the [[Scottish Professional Football League]] after the Scottish Football League merged with the [[Scottish Premier League]] in 2013. One change at this time was that the two invitational places were split, with only one place filled by a Highland League club (with a valid SFA club licence) and the other place going to the winner of a preliminary round tie between clubs from the [[East of Scotland League]] and the [[South of Scotland League]].<ref>{{cite web |url=http://sport.stv.tv/football/clubs/rangers/231200-rangers-to-travel-to-face-albion-rovers-in-ramsdens-cup-first-round/ |title=Rangers to travel to face Albion Rovers in Ramsdens Cup first round |work=sport.stv.tv |publisher=STV |date=28 June 2013 |access-date=11 April 2014}}</ref> This was simplified in the 2014–15 season, with the two additional places going to the Highland League champion ([[Brora Rangers F.C.|Brora Rangers]]) and the Lowland League champion ([[Spartans F.C.|Spartans]]).<ref name=brora>[https://www.bbc.co.uk/sport/0/football/28115445 Scottish Challenge Cup gets new sponsorship deal], BBC Sport.</ref> From 2016 to 2017 the competition has been further expanded with the addition of [[Scottish Premiership]] [[SPFL Development League|Under-20 teams]], additional places for the Highland and Lowland Leagues, which now have four representatives each, as well as the top two teams from Northern Ireland and Wales.<ref name="SPFL Format" /> The top two teams not to qualify for European competition from the [[League of Ireland]] were included in the competition for the 2017&ndash;18 season.<ref>{{cite web |url=https://www.bbc.co.uk/sport/football/38974097 |title=Sligo Rovers and Bray in next season's Scottish Challenge Cup |publisher=BBC Sport  |date=14 February 2017 |access-date=14 February 2017}}</ref>

From [[2018–19 Scottish Challenge Cup|2018–19]], the competition was further expanded with the two highest ranked teams still remaining in England's [[National League (English football)|National League]] to take part from the second round. The first English teams to compete were [[Sutton United F.C.|Sutton United]] and [[Boreham Wood F.C.|Boreham Wood]].<ref>{{Cite web|url=https://spfl.co.uk/news/article/national-league-sides-join-irn-bru-cup/|title=National League sides join IRN-BRU Cup – Scottish Professional Football League|website=spfl.co.uk|language=en-GB|access-date=2018-06-08|archive-date=12 June 2018|archive-url=https://web.archive.org/web/20180612143325/https://spfl.co.uk/news/article/national-league-sides-join-irn-bru-cup/|url-status=dead}}</ref> The age level was raised for colts teams from under-20 to under-21 in a rule change introduced by the [[SPFL]] ahead of 2018–19 competition.<ref>{{cite web | url=https://spfl.co.uk/news/irn-bru-cup-rule-changes-announced | title=IRN-BRU CUP RULE CHANGES ANNOUNCED | publisher=[[SPFL]] | date=27 June 2018 | access-date=21 May 2019}}</ref> The 2018–19 final also saw [[Connah's Quay Nomads F.C.|Connah's Quay Nomads]] become the first non-Scottish side to play in the final.

The [[COVID-19 pandemic in Scotland]] had a significant impact on the competition.<ref name = covid/> The [[2020 Scottish Challenge Cup Final|2019&ndash;20 final]], between [[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]] and [[Raith Rovers F.C.|Raith Rovers]], was originally scheduled for 28 March 2020 but was postponed and later cancelled, with the teams sharing the title.<ref name = covid/><ref>{{cite web |url=https://www.bbc.co.uk/sport/football/56945120 |title=Inverness Caledonian Thistle and Raith Rovers share last season's Scottish Challenge Cup |website=BBC Sport |date=30 April 2021 |accessdate=30 April 2021}}</ref> Continuing restrictions on fans entering stadiums meant that the competition was unviable for most SPFL clubs, and the scheduled 2020&ndash;21 edition was cancelled in October 2020. It was announced in May 2021, that only Scottish clubs would participate in [[2021–22 Scottish Challenge Cup|2021&ndash;22]] due to the coronavirus pandemic.<ref name = covid>{{cite web |url=https://www.bbc.co.uk/sport/football/54393418 |title=Scottish Challenge Cup cancelled for season 2020-21 |publisher=BBC Sport  |date=2 October 2020 |access-date=3 October 2020}}</ref>

In 2024, it was announced that the format following the conclusion of the 2024–25 edition of the cup would change, where non-Scottish teams would no longer participate, whilst, controversially, the Premiership B Teams would still take part.

== Venues ==
[[File:McDiarmid Park.jpg|thumb|right |225px |alt=The interior of a football stadium from a spectator stand |McDiarmid Park in Perth has hosted the final 10 times, more times than any other venue.]]
In the rounds before the final, the venue of each match is determined when the fixtures are drawn; the first club drawn in a fixture is named the home team and chooses the venue for the match, usually its own [[Home (sports)|home ground]].<ref name="SFL_Format" /> The venue may be switched to that of the [[Road (sports)|away team]] or changed to a neutral venue for security reasons such as being unable to host a club with a large travelling fan base or the venue being unavailable.<ref name="Glebe_Park_Rangers">{{cite news |url=http://www.scotsman.com/sport/football/top-football-stories/rangers-to-kick-off-season-with-ramsdens-cup-tie-at-brechin-1-2416280 |title=Rangers to kick off season with Ramsdens Cup tie at Brechin |newspaper=[[The Scotsman]] |date=17 July 2012 |access-date=6 April 2013}}</ref><ref name="Broadwood_unavailable">[http://www.clydefc.co.uk/news/2012/06/12/4128/#.UWA5u0paaLY Ramsdens Cup Draw], ''clydefc.co.uk''. [[Clyde F.C.]] 12 June 2012. Retrieved 6 April 2013.</ref>

=== Final venue ===
The final match of the tournament is played at a [[neutral venue]], usually one that is geographically close or equidistant to where the clubs contesting the match are based. As of 2024, eleven different venues have hosted the final. [[Fir Park]] in [[Motherwell]] was the first, in [[1990 Scottish Challenge Cup Final|1990]], and has since hosted four more finals, the last in [[2017 Scottish Challenge Cup Final|2017]].<ref name="SFHA_Challenge_Cup" /> [[McDiarmid Park]] in [[Perth, Scotland|Perth]] has been the most frequent venue, staging it ten times between [[1994 Scottish Challenge Cup Final|1994]] and [[2018 Scottish Challenge Cup Final|2018]]. Other venues to host the final more than once are [[Broadwood Stadium]] ([[Cumbernauld]]), [[Excelsior Stadium]] ([[Airdrie, North Lanarkshire|Airdrie]]), [[Almondvale Stadium]] ([[Livingston, West Lothian|Livingston]]) and [[Falkirk Stadium]] ([[Falkirk]]).<ref name="BBC_Livingston_final_venue">[https://www.bbc.co.uk/sport/0/football/20184286 Livingston to host Ramsdens Cup final for a consecutive season]. [[BBC Sport]]. 2 November 2012. Retrieved 6 April 2013.</ref> The [[2016 Scottish Challenge Cup Final|2016 final]] was held at [[Hampden Park]], the national stadium in [[Glasgow]], due to the large support of eventual winners [[Rangers F.C.|Rangers]];<ref>{{cite news|title=Challenge Cup final: Hampden to stage Rangers v Peterhead|url=https://www.bbc.co.uk/sport/football/35105603|access-date=10 April 2016|publisher=BBC Sport|date=15 December 2015}}</ref> that final drew the competition's record attendance of over 48,000.<ref name=final16>{{cite web|title=Rangers 4-0 Peterhead|url=https://www.bbc.co.uk/sport/football/35953055|access-date=8 June 2018|publisher=BBC Sport|date=10 April 2016}}</ref>

== Winners and finalists ==
<!--As of the 2025 final-->A total of 28 clubs have reached the final, of whom 17 have won the competition. The first winners were [[Dundee F.C.|Dundee]] in [[1990 Scottish Challenge Cup Final|1990]].<ref name="SFL_Final_Results" /> The most successful club is [[Falkirk F.C.|Falkirk]] with four wins from four final appearances.<ref name="statto_honours">[http://www.statto.com/football/stats/scotland/challenge-cup/honours Scottish Challenge Cup Honours], ''statto.com''. Retrieved 6 April 2013.</ref> [[Ross County F.C.|Ross County]], [[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]], [[Queen of the South F.C.|Queen of the South]] and [[Hamilton Academical F.C.|Hamilton Academical]] are the only four clubs to have reached the final five times, Ross County and Hamilton Academical winning on three occasions, Inverness Caledonian Thistle winning two and sharing one and Queen of the South winning twice and losing thrice. Four clubs have reached the final in successive seasons; [[Ayr United F.C.|Ayr United]] did so in the first two years of the tournament but lost both, Hamilton Academical and the original Airdrieonians defending their titles in 1992 and 1993, and 2001 and 2001, respectively, and Raith Rovers,who are the only team to make three finals in a row, sharing their first with [[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]] in April 2021, due to the [[COVID-19 pandemic|COVID-19 Pandemic]] cancelling the match, before defeating [[Queen of the South F.C.|Queen of the South]] in the following final in [[2021–22 Scottish Challenge Cup|2021–22]], then losing the third against Hamilton Academical in 2023. It is possible for the winner of the tournament to be unable to defend their title; if a club is promoted from the [[Scottish Championship]] (second tier) in the same season to the [[Scottish Premiership]] (first tier), the club becomes ineligible to compete in the tournament. This has happened to [[Falkirk F.C.|Falkirk]] twice; in 1994 and 2005, [[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]] in 2004, [[Livingston F.C.|Livingston]] in 2025, [[St Mirren F.C.|St Mirren]] in 2006, [[Rangers F.C.|Rangers]] in 2016, and [[Ross County F.C.|Ross County]] in 2019.

Most winners and finalists have been from the second tier, while only four teams have won the competition from below this division. [[Stenhousemuir F.C.|Stenhousemuir]] became the first team to do so in [[1995 Scottish Challenge Cup Final|1995]], followed by [[Stranraer F.C.|Stranraer]] a year later in [[1996 Scottish Challenge Cup Final|1996]] and [[Alloa Athletic F.C.|Alloa Athletic]] in [[1999 Scottish Challenge Cup Final|1999]]. The most recent club to win from below the second tier was [[Queen of the South F.C.|Queen of the South]], in [[2013 Scottish Challenge Cup Final|2013]].<ref name="BBC_2013_Final">[https://www.bbc.co.uk/sport/0/football/22043859 Queen of the South 1-1 Partick Thistle (6-5 pens)]. [[BBC Sport]]. 7 April 2013. Retrieved 7 April 2013.</ref> All winners and runners-up from below the second tier have been from the [[Scottish League One|third tier]].

In 2019, [[Connah's Quay Nomads F.C.|Connah's Quay Nomads]] of Wales were the first non-Scottish side to reach the final of the Scottish Challenge Cup; despite taking the lead in the 21st minute, they eventually lost 3–1 to [[Ross County F.C.|Ross County]]. In 2024, another Welsh side, [[The New Saints F.C.|The New Saints]] also made the final of the Challenge Cup, becoming the second non foreign side to achieve this feat, however, like Connah's Quay, fell to defeat after taking an early lead, eventually losing 2–1 to [[Airdrieonians F.C.|Airdrieonians]]. They would become the last foreign side to reach the final, as the format for the following seasons would not include non-Scottish sides.

== Finals ==
The winner of the tournament is decided by a [[Final (competition)|final elimination match]] which lasts 90 minutes plus any additional [[stoppage time]].<ref name="SFL_Format">[http://www.scottishfootballleague.com/football/challenge-cup/format/ Format], ''scottishfootballleague.com''. [[Scottish Football League]]. Retrieved 4 April 2013.</ref> If the score is level and a winner has not been determined after 90 minutes of normal time, 30 minutes of [[extra time]] is played, followed by a [[penalty shoot-out (association football)|penalty shoot-out]] if the score is still level.<ref name="SFL_Format" /> Eight finals have gone to extra time, with two being decided in this period of play. The further six have been decided by penalty shoot-out.<ref name="SLCC_finals_RSSSF" />
{| class="wikitable"
|+Key to list of finals
|-
|align=center style="background-color:#cef2e0"|*
|Match went to [[extra time]]
|-
|align=center style="background-color:#cedff2"|{{dagger}}
|Match decided by a [[Penalty shoot-out (association football)|penalty shoot-out]] after extra time
|-
|align=center style="background-color:#fff4a7"|{{double dagger}}
|Winning team won the second tier of [[Scottish football league system]]
|-
|''Italics''
|Team from below the second tier of the [[Scottish football league system]]
|-
|{{Flagicon|ENG}}, {{Flagicon|WAL}}, {{Flagicon|NIR}}, or {{Flagicon|IRE}}
|Team from outside the [[Scottish football league system]]
|}

=== Results ===
{| class="sortable plainrowheaders wikitable"
|+Scottish Challenge Cup finals
|-
!scope=col|Season
!scope=col|Winner<ref name="SLCC_finals_RSSSF">[https://www.rsssf.org/tabless/scotchcuphist.html Scottish League Challenge Cup Finals], ''rsssf.com''. [[Rec.Sport.Soccer Statistics Foundation|RSSSF]]. 2 December 2009. Retrieved 4 April 2013.</ref><ref>[https://spfl.co.uk/news/previous-irn-bru-cup-finals PREVIOUS IRN-BRU CUP FINALS], [[Scottish Professional Football League|SPFL]]. 2 1 March 2019. Retrieved 21 May 2019.</ref>
!scope=col|Score<ref name="SLCC_finals_RSSSF" /><ref name="SFL_Bell's_Cup" />
!scope=col|Runner-up<ref name="SLCC_finals_RSSSF" /><ref name="SFL_Bell's_Cup" />
!scope=col|Venue<ref name="SFL_Bell's_Cup">[http://www.scottishfootballleague.com/news/article/the-league-challenge-cup-final-resu/ Bell's Cup], ''scottishfootballleague.com''. [[Scottish Football League]]. 2 November 2005. Retrieved 4 April 2013.</ref>
!scope=col|Attendance<ref name="SFL_Bell's_Cup" />
|-
!scope=row style=text-align:center|[[1990–91 Scottish Challenge Cup|1990–91]]
|[[Dundee F.C.|Dundee]]
|style="background:#cef2e0;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[1990 Scottish Challenge Cup final|3–2]] *
|[[Ayr United F.C.|Ayr United]]
|[[Fir Park]]
|align=center|11,506
|-
!scope=row style=text-align:center|[[1991–92 Scottish Challenge Cup|1991–92]]
|[[Hamilton Academical F.C.|Hamilton Academical]]
|align=center|[[1991 Scottish Challenge Cup final|1–0]]
|[[Ayr United F.C.|Ayr United]]
|[[Fir Park]]
|align=center|9,663
|-
!scope=row style=text-align:center|[[1992–93 Scottish Challenge Cup|1992–93]]
|[[Hamilton Academical F.C.|Hamilton Academical]]
|align=center|[[1992 Scottish Challenge Cup final|3–2]]
|[[Greenock Morton F.C.|Morton]]
|[[Love Street (stadium)|Love Street]]
|align=center|7,391
|-
!scope=row style=text-align:center|[[1993–94 Scottish Challenge Cup|1993–94]]
|style="background:#fff4a7;"|[[Falkirk F.C.|Falkirk]] {{double-dagger}}
|align=center|[[1993 Scottish Challenge Cup final|3–0]]
|[[St Mirren F.C.|St Mirren]]
|[[Fir Park]]
|align=center|13,763
|-
!scope=row style=text-align:center|[[1994–95 Scottish Challenge Cup|1994–95]]
|[[Airdrieonians F.C. (1878)|Airdrieonians]]
|style="background:#cef2e0;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[1994 Scottish Challenge Cup final|3–2]] *
|[[Dundee F.C.|Dundee]]
|[[McDiarmid Park]]
|align=center|8,844
|-
!scope=row style=text-align:center|[[1995–96 Scottish Challenge Cup|1995–96]]
|''[[Stenhousemuir F.C.|Stenhousemuir]]''
|style="background:#cedff2;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[1995 Scottish Challenge Cup final|0–0]] †
|[[Dundee United F.C.|Dundee United]]
|[[McDiarmid Park]]
|align=center|7,856
|-
!scope=row style=text-align:center|[[1996–97 Scottish Challenge Cup|1996–97]]
|''[[Stranraer F.C.|Stranraer]]''
|align=center|[[1996 Scottish Challenge Cup final|1–0]]
|[[St Johnstone F.C.|St Johnstone]]
|[[Broadwood Stadium]]
|align=center|5,222
|-
!scope=row style=text-align:center|[[1997–98 Scottish Challenge Cup|1997–98]]
|[[Falkirk F.C.|Falkirk]]
|align=center|[[1997 Scottish Challenge Cup final|1–0]]
|''[[Queen of the South F.C.|Queen of the South]]''
|[[Fir Park]]
|align=center|9,735
|-class="sortbottom"
!scope=row style=text-align:center|1998–99
|colspan="5" style="text-align:center;"|''Competition suspended due to lack of sponsorship''
|-
!scope=row style=text-align:center|[[1999–2000 Scottish Challenge Cup|1999–2000]]
|''[[Alloa Athletic F.C.|Alloa Athletic]]''
|style="background:#cedff2;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[1999 Scottish Challenge Cup final|4–4]] †
|[[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]]
|[[Excelsior Stadium]]
|align=center|4,043
|-
!scope=row style=text-align:center|[[2000–01 Scottish Challenge Cup|2000–01]]
|[[Airdrieonians F.C. (1878)|Airdrieonians]]
|style="background:#cedff2;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[2000 Scottish Challenge Cup final|2–2]] †
|[[Livingston F.C.|Livingston]]
|[[Broadwood Stadium]]
|align=center|5,623
|-
!scope=row style=text-align:center|[[2001–02 Scottish Challenge Cup|2001–02]]
|[[Airdrieonians F.C. (1878)|Airdrieonians]]
|align=center|[[2001 Scottish Challenge Cup final|2–1]]
|''[[Alloa Athletic F.C.|Alloa Athletic]]''
|[[Broadwood Stadium]]
|align=center|4,548
|-
!scope=row style=text-align:center|[[2002–03 Scottish Challenge Cup|2002–03]]
|[[Queen of the South F.C.|Queen of the South]]
|align=center|[[2002 Scottish Challenge Cup final|2–0]]
|''[[Brechin City F.C.|Brechin City]]''
|[[Broadwood Stadium]]
|align=center|6,428
|-
!scope=row style=text-align:center|[[2003–04 Scottish Challenge Cup|2003–04]]
|style="background:#fff4a7;"|[[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]] {{double dagger}}
|align=center|[[2003 Scottish Challenge Cup final|2–0]]
|''[[Airdrie United F.C.|Airdrie United]]''
|[[McDiarmid Park]]
|align=center|5,428
|-
!scope=row style=text-align:center|[[2004–05 Scottish Challenge Cup|2004–05]]
|style="background:#fff4a7;"|[[Falkirk F.C.|Falkirk]] {{double dagger}}
|align=center|[[2004 Scottish Challenge Cup final|2–1]]
|[[Ross County F.C.|Ross County]]
|[[McDiarmid Park]]
|align=center|7,471
|-
!scope=row style=text-align:center|[[2005–06 Scottish Challenge Cup|2005–06]]
|style="background:#fff4a7;"|[[St Mirren F.C.|St Mirren]] {{double dagger}}
|align=center|[[2005 Scottish Challenge Cup final|2–1]]
|[[Hamilton Academical F.C.|Hamilton Academical]]
|[[Excelsior Stadium]]
|align=center|9,613
|-
!scope=row style=text-align:center|[[2006–07 Scottish Challenge Cup|2006–07]]
|[[Ross County F.C.|Ross County]]
|style="background:#cedff2;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[2006 Scottish Challenge Cup final|1–1]] †
|[[Clyde F.C.|Clyde]]
|[[McDiarmid Park]]
|align=center|4,062
|-
!scope=row style=text-align:center|[[2007–08 Scottish Challenge Cup|2007–08]]
|[[St Johnstone F.C.|St Johnstone]]
|align=center|[[2007 Scottish Challenge Cup final|3–2]]
|[[Dunfermline Athletic F.C.|Dunfermline Athletic]]
|[[Dens Park]]
|align=center|6,446
|-
!scope=row style=text-align:center|[[2008–09 Scottish Challenge Cup|2008–09]]
|[[Airdrie United F.C.|Airdrie United]]
|style="background:#cedff2;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[2008 Scottish Challenge Cup final|2–2]] †
|[[Ross County F.C.|Ross County]]
|[[McDiarmid Park]]
|align=center|4,091
|-
!scope=row style=text-align:center|[[2009–10 Scottish Challenge Cup|2009–10]]
|[[Dundee F.C.|Dundee]]
|align=center|[[2009 Scottish Challenge Cup final|3–2]]
|[[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]]
|[[McDiarmid Park]]
|align=center|8,031
|-
!scope=row style=text-align:center|[[2010–11 Scottish Challenge Cup|2010–11]]
|[[Ross County F.C.|Ross County]]
|align=center|[[2010 Scottish Challenge Cup final|2–0]]
|[[Queen of the South F.C.|Queen of the South]]
|[[McDiarmid Park]]
|align=center|5,124
|-
!scope=row style=text-align:center|[[2011–12 Scottish Challenge Cup|2011–12]]
|[[Falkirk F.C.|Falkirk]]
|align=center|[[2012 Scottish Challenge Cup final|1–0]]
|[[Hamilton Academical F.C.|Hamilton Academical]]
|[[Almondvale Stadium]]
|align=center|5,210
|-
!scope=row style=text-align:center|[[2012–13 Scottish Challenge Cup|2012–13]]
|''[[Queen of the South F.C.|Queen of the South]]''
|style="background:#cedff2;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[2013 Scottish Challenge Cup final|1–1]] †
|[[Partick Thistle F.C.|Partick Thistle]]
|[[Almondvale Stadium]]
|align=center|9,452
|-
!scope=row style=text-align:center|[[2013–14 Scottish Challenge Cup|2013–14]]
|[[Raith Rovers F.C.|Raith Rovers]]
|style="background:#cef2e0;" align=center|<span style="visibility:hidden;color: transparent">&nbsp;†</span>[[2014 Scottish Challenge Cup final|1–0]] *
|[[Rangers F.C.|Rangers]]
|[[Easter Road]]
|align=center|19,983
|-
!scope=row style=text-align:center|[[2014–15 Scottish Challenge Cup|2014–15]]
|[[Livingston F.C.|Livingston]]
|align=center|[[2015 Scottish Challenge Cup final|4–0]]
|[[Alloa Athletic F.C.|Alloa Athletic]]
|[[McDiarmid Park]]
|align=center|2,869
|-
!scope=row style=text-align:center|[[2015–16 Scottish Challenge Cup|2015–16]]
|style="background:#fff4a7;"|[[Rangers F.C.|Rangers]] {{double-dagger}}
|align=center|[[2016 Scottish Challenge Cup final|4–0]]
|''[[Peterhead F.C.|Peterhead]]''
|[[Hampden Park]]
|align=center|48,133<ref name=final16/>
|-
!scope=row style=text-align:center|[[2016–17 Scottish Challenge Cup|2016–17]]
|[[Dundee United F.C.|Dundee United]]
|align=center|[[2017 Scottish Challenge Cup final|2–1]]
|[[St Mirren F.C.|St Mirren]] 
|[[Fir Park]]
|align=center|8,089
|-
!scope=row style=text-align:center|[[2017–18 Scottish Challenge Cup|2017–18]]
|[[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]]
|align=center|[[2018 Scottish Challenge Cup final|1–0]]
|[[Dumbarton F.C.|Dumbarton]] 
|[[McDiarmid Park]]
|align=center|4,602
|-
!scope=row style=text-align:center|[[2018–19 Scottish Challenge Cup|2018–19]]
|style="background:#fff4a7;"|[[Ross County F.C.|Ross County]] {{double-dagger}}
|align=center|[[2019 Scottish Challenge Cup final|3–1]] 
|{{Flagicon|WAL}} [[Connah's Quay Nomads F.C.|Connah's Quay Nomads]]
|[[Caledonian Stadium]]
|align=center|3,057
|-
!scope=row style=text-align:center|[[2019–20 Scottish Challenge Cup|2019–20]]
|colspan="5" style="text-align:center;"|[[2020 Scottish Challenge Cup final|Final]] match not played; trophy shared by [[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]] and [[Raith Rovers F.C.|Raith Rovers]]<ref>{{cite web |url=https://www.bbc.co.uk/sport/football/56945120 |title=Inverness Caledonian Thistle and Raith Rovers share last season's Scottish Challenge Cup |publisher=BBC Sport |date=30 April 2021 |access-date=30 April 2021}}</ref>
|-
!scope=row style=text-align:center|2020–21
|colspan="5" style="text-align:center;"|''Tournament cancelled''<ref name = covid/>
|-
!scope=row style=text-align:center|[[2021–22 Scottish Challenge Cup|2021–22]]
|[[Raith Rovers F.C.|Raith Rovers]]
|align=center|[[2022 Scottish Challenge Cup final|3–1]]
|[[Queen of the South F.C.|Queen of the South]]
|[[Excelsior Stadium]] 
|align=center|4,452
|-
!scope=row style=text-align:center|[[2022–23 Scottish Challenge Cup|2022–23]]
|[[Hamilton Academical F.C.|Hamilton Academical]]
|align=center|[[2023 Scottish Challenge Cup final|1–0]]
|[[Raith Rovers F.C.|Raith Rovers]]
|[[Falkirk Stadium]]
|align=center|5,566
|-
!scope=row style=text-align:center|[[2023–24 Scottish Challenge Cup|2023–24]]
|[[Airdrieonians F.C.|Airdrieonians]]
|align=center|[[2024 Scottish Challenge Cup final|2–1]]
|{{Flagicon|WAL}} [[The New Saints F.C.|The New Saints]]
|[[Falkirk Stadium]]
|align=center|3,191
|-
!scope=row style=text-align:center|[[2024–25 Scottish Challenge Cup|2024–25]]
|[[Livingston F.C.|Livingston]]
|align=center|[[2025 Scottish Challenge Cup final|5–0]]
|[[Queen's Park F.C.|Queen's Park]]
|[[Falkirk Stadium]]
|align=center|4,079
|}

=== Performance by club ===
{| class="wikitable sortable plainrowheaders" style="text-align: center;"
|+Performance by club
!scope="col"| Club
!scope="col"| Wins
!scope="col"| Last final won
!scope="col"| Runners-up
!scope="col"| Last final lost
!scope="col"| Total final appearances
|-
!scope="row"|[[Falkirk F.C.|Falkirk]]
|4
|[[2012 Scottish Challenge Cup final|2012]]
|0
|—
|4
|-
!scope="row"|[[Hamilton Academical F.C.|Hamilton Academical]]
|3
|[[2023 Scottish Challenge Cup final|2023]]
|2
|[[2012 Scottish Challenge Cup final|2012]]
|5
|-
! scope="row" |[[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]]
|3
|[[2020 Scottish Challenge Cup final|2020]]*
|2
|[[2009 Scottish Challenge Cup final|2009]]
|5
|-
!scope="row"|[[Ross County F.C.|Ross County]]
|3
|[[2019 Scottish Challenge Cup final|2019]]
|2
|[[2008 Scottish Challenge Cup final|2008]]
|5 
|-
! scope="row" |[[Raith Rovers F.C.|Raith Rovers]]
|3
|[[2020 Scottish Challenge Cup final|2022]]
|1
|[[2023 Scottish Challenge Cup final|2023]]
|4
|-
!scope="row"|''[[Airdrieonians F.C. (1878)|Airdrieonians (1878)]]''
|3
|[[2001 Scottish Challenge Cup final|2001]]
|0
|—
|3
|-
!scope="row"|[[Queen of the South F.C.|Queen of the South]]
|2
|[[2013 Scottish Challenge Cup final|2013]]
|3
|[[2010 Scottish Challenge Cup final|2022]]
|5
|-
!scope="row"|[[Dundee F.C.|Dundee]]
|2
|[[2009 Scottish Challenge Cup final|2009]]
|1
|[[1994 Scottish Challenge Cup final|1994]]
|3
|-
!scope="row"|[[Airdrieonians F.C.|Airdrieonians]]
|2
|[[2024 Scottish Challenge Cup final|2024]]
|1
|[[2003 Scottish Challenge Cup final|2003]]
|3
|-
!scope="row"|[[Livingston F.C.|Livingston]]
|2
|[[2025 Scottish Challenge Cup final|2025]]
|1
|[[2000 Scottish Challenge Cup final|2000]]
|3
|-
!scope="row"|[[St Mirren F.C.|St Mirren]]
|1
|[[2005 Scottish Challenge Cup final|2005]]
|2
|[[2017 Scottish Challenge Cup final|2017]]
|3
|-
!scope="row"|[[Alloa Athletic F.C.|Alloa Athletic]]
|1
|[[1999 Scottish Challenge Cup final|1999]]
|2
|[[2015 Scottish Challenge Cup final|2015]]
|3
|-
!scope="row"|[[Dundee United F.C.|Dundee United]]
|1
|[[2017 Scottish Challenge Cup final|2017]]
|1
|[[1995 Scottish Challenge Cup final|1995]]
|2
|-
!scope="row"|[[Rangers F.C.|Rangers]]
|1
|[[2016 Scottish Challenge Cup final|2016]]
|1
|[[2014 Scottish Challenge Cup final|2014]]
|2
|-
!scope="row"|[[St Johnstone F.C.|St Johnstone]]
|1
|[[2007 Scottish Challenge Cup final|2007]]
|1
|[[1996 Scottish Challenge Cup final|1996]]
|2
|-
!scope="row"|[[Stranraer F.C.|Stranraer]]
|1
|[[1996 Scottish Challenge Cup final|1996]]
|0
|—
|1
|-
!scope="row"|[[Stenhousemuir F.C.|Stenhousemuir]]
|1
|[[1995 Scottish Challenge Cup final|1995]]
|0
|—
|1
|-
!scope="row"|[[Ayr United F.C.|Ayr United]]
|0
|—
|2
|[[1991 Scottish Challenge Cup final|1991]]
|2
|-
!scope="row"|[[Queen's Park F.C.|Queen's Park]]
|0
|—
|1
|[[2025 Scottish Challenge Cup final|2025]]
|1
|-
!scope="row"|{{Flagicon|WAL}} [[The New Saints F.C.|The New Saints]]
|0
|—
|1
|[[2024 Scottish Challenge Cup final|2024]]
|1
|-
!scope="row"|{{Flagicon|WAL}} [[Connah's Quay Nomads F.C.|Connah's Quay Nomads]]
|0
|—
|1
|[[2019 Scottish Challenge Cup final|2019]]
|1
|-
!scope="row"|[[Dumbarton F.C.|Dumbarton]]
|0
|—
|1
|[[2018 Scottish Challenge Cup final|2018]]
|1
|-
!scope="row"|[[Peterhead F.C.|Peterhead]]
|0
|—
|1
|[[2016 Scottish Challenge Cup final|2016]]
|1
|-
!scope="row"|[[Partick Thistle F.C.|Partick Thistle]]
|0
|—
|1
|[[2013 Scottish Challenge Cup final|2013]]
|1
|-
!scope="row"|[[Dunfermline Athletic F.C.|Dunfermline Athletic]]
|0
|—
|1
|[[2007 Scottish Challenge Cup final|2007]]
|1
|-
!scope="row"|[[Clyde F.C.|Clyde]]
|0
|—
|1
|[[2006 Scottish Challenge Cup final|2006]]
|1
|-
!scope="row"|[[Brechin City F.C.|Brechin City]]
|0
|—
|1
|[[2002 Scottish Challenge Cup final|2002]]
|1
|-
!scope="row"|[[Greenock Morton F.C.|Morton]]
|0
|—
|1
|[[1992 Scottish Challenge Cup final|1992]]
|1
|-
|}

== List of winning managers ==
{| class="sortable plainrowheaders wikitable"
|+List of winning managers
|-
! scope=col width=10%| Season
! scope=col width=15%| Manager<ref>{{cite web | url=http://spfl.co.uk/news/article/petrofac-cup-winning-managers/ | title=Petrofac Cup: Winning managers | publisher=[[Scottish Professional Football League|SPFL]] | date=5 April 2016 | access-date=12 April 2017}}<br />{{cite web | url=http://spfl.co.uk/news/article/irn-bru-cup-winning-managers/ | title=Irn–Bru Cup: Winning managers | publisher=[[Scottish Professional Football League|SPFL]] | date=21 March 2017 | access-date=12 April 2017}}<br />{{cite web | url=https://spfl.co.uk/news/challenge-cup-winning-bosses | title=IRN-BRU CUP WINNING BOSSES | publisher=[[Scottish Professional Football League|SPFL]] | date=20 March 2019 | access-date=20 March 2019}}</ref>
! scope=col width=5%| Nationality
! scope=col| Club
! scope=col| Notes
|-
! scope=row style=text-align:center| [[1990–91 Scottish Challenge Cup|1990–91]]
| {{sortname|Gordon|Wallace|dab=footballer, born 1943}}
| Scotland
| [[Dundee F.C.|Dundee]]
| 
|-
! scope=row style=text-align:center| [[1991–92 Scottish Challenge Cup|1991–92]]
| {{sortname|Billy|McLaren}}
| Scotland
| [[Hamilton Academical F.C.|Hamilton Academical]]
|
|-
! scope=row style=text-align:center| [[1992–93 Scottish Challenge Cup|1992–93]]
| {{sortname|Iain|Munro}}
| Scotland
| [[Hamilton Academical F.C.|Hamilton Academical]]
|
|-
! scope=row style=text-align:center| [[1993–94 Scottish Challenge Cup|1993–94]]
| {{sortname|Jim|Jefferies|dab=footballer}}
| Scotland
| [[Falkirk F.C.|Falkirk]]
|
|-
! scope=row style=text-align:center| [[1994–95 Scottish Challenge Cup|1994–95]]
| {{sortname|Alex|MacDonald|dab=footballer, born 1948}}
| Scotland
| [[Airdrieonians F.C. (1878)|Airdrieonians]]
|
|-
! scope=row style=text-align:center| [[1995–96 Scottish Challenge Cup|1995–96]]
| {{sortname|Terry|Christie}}
| Scotland
| [[Stenhousemuir F.C.|Stenhousemuir]]
| First manager to win the competition with a club outside of the [[List of winners of the Scottish Championship and predecessors|second tier]].
|-
! scope=row style=text-align:center| [[1996–97 Scottish Challenge Cup|1996–97]]
| {{sortname|Campbell|Money}}
| Scotland
| [[Stranraer F.C.|Stranraer]]
| 
|-
! scope=row style=text-align:center| [[1997–98 Scottish Challenge Cup|1997–98]]
| {{sortname|Alex|Totten}}
| Scotland
| [[Falkirk F.C.|Falkirk]]
|
|-
! scope=row style=text-align:center| [[1999–2000 Scottish Challenge Cup|1999–2000]]
| {{sortname|Terry|Christie}} (2)
| Scotland
| [[Alloa Athletic F.C.|Alloa Athletic]]
| First manager to win the competition more than once, with two different clubs.
|-
! scope=row style=text-align:center| [[2000–01 Scottish Challenge Cup|2000–01]]
| {{sortname|Steve|Archibald}}
| Scotland
| [[Airdrieonians F.C. (1878)|Airdrieonians]]
|
|-
! scope=row style=text-align:center| [[2001–02 Scottish Challenge Cup|2001–02]]
| {{sortname|Ian|McCall|dab=footballer}}
| Scotland
| [[Airdrieonians F.C. (1878)|Airdrieonians]]
|
|-
! scope=row style=text-align:center| [[2002–03 Scottish Challenge Cup|2002–03]]
| {{sortname|John|Connolly|dab=Scottish footballer}}
| Scotland
| [[Queen of the South F.C.|Queen of the South]]
|
|-
! scope=row style=text-align:center| [[2003–04 Scottish Challenge Cup|2003–04]]
| {{sortname|John|Robertson|dab=footballer, born 1964}}
| Scotland
| {{nowrap|[[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]]}}
|
|-
! scope=row style=text-align:center| [[2004–05 Scottish Challenge Cup|2004–05]]
| {{sortname|John|Hughes|dab=footballer, born 1964}}
| Scotland
| [[Falkirk F.C.|Falkirk]]
|
|-
! scope=row style=text-align:center| [[2005–06 Scottish Challenge Cup|2005–06]]
| {{sortname|Gus|MacPherson}}
| Scotland
| [[St Mirren F.C.|St Mirren]]
|
|-
! scope=row style=text-align:center| [[2006–07 Scottish Challenge Cup|2006–07]]
| {{sortname|Scott|Leitch}}
| Scotland
| [[Ross County F.C.|Ross County]]
|
|-
! scope=row style=text-align:center| [[2007–08 Scottish Challenge Cup|2007–08]]
| {{sortname|Sandy|Stewart|dab=footballer}}
| Scotland
| [[St Johnstone F.C.|St Johnstone]]
| 
|-
! scope=row style=text-align:center| [[2008–09 Scottish Challenge Cup|2008–09]]
| {{sortname|Kenny|Black}}
| Scotland
| [[Airdrie United F.C.|Airdrie United]]
|
|-
! scope=row style=text-align:center| [[2009–10 Scottish Challenge Cup|2009–10]]
| {{sortname|Jocky|Scott}}
| Scotland
| [[Dundee F.C.|Dundee]]
|
|-
! scope=row style=text-align:center| [[2010–11 Scottish Challenge Cup|2010–11]]
| {{sortname|Jimmy|Calderwood}}
| Scotland
| [[Ross County F.C.|Ross County]]
|
|-
! scope=row style=text-align:center| [[2011–12 Scottish Challenge Cup|2011–12]]
| {{sortname|Steven|Pressley}}
| Scotland
| [[Falkirk F.C.|Falkirk]]
|
|-
! scope=row style=text-align:center| [[2012–13 Scottish Challenge Cup|2012–13]]
| {{sortname|Allan|Johnston}}
| Scotland
| [[Queen of the South F.C.|Queen of the South]]
| 
|-
! scope=row style=text-align:center| [[2013–14 Scottish Challenge Cup|2013–14]]
| {{sortname|Grant|Murray}}
| Scotland
| [[Raith Rovers F.C.|Raith Rovers]]
|
|-
! scope=row style=text-align:center| [[2014–15 Scottish Challenge Cup|2014–15]]
| {{sortname|Mark|Burchill}}
| Scotland
| [[Livingston F.C.|Livingston]]
| 
|-
! scope=row style=text-align:center| [[2015–16 Scottish Challenge Cup|2015–16]]
| {{sortname|Mark|Warburton}}
| England
| [[Rangers F.C.|Rangers]]
| First non-Scottish manager to win the competition.
|-
! scope=row style=text-align:center| [[2016–17 Scottish Challenge Cup|2016–17]]
| {{sortname|Ray|McKinnon|dab=footballer}}
| Scotland
| [[Dundee United F.C.|Dundee United]]
|
|-
! scope=row style=text-align:center| [[2017–18 Scottish Challenge Cup|2017–18]]
| {{sortname|John|Robertson|dab=footballer, born 1964}} (2)
| Scotland
| [[Inverness Caledonian Thistle F.C.|Inverness Caledonian Thistle]]
| First manager to win the cup more than once with the same club.
|-
! scope=row style=text-align:center| [[2018–19 Scottish Challenge Cup|2018–19]]
| [[Steve Ferguson (footballer)|Steven Ferguson]]<br>[[Stuart Kettlewell]]
| Scotland
| [[Ross County F.C.|Ross County]]
| First co-managers to win the cup
|-
! scope=row style=text-align:center rowspan="2" |[[2019–20 Scottish Challenge Cup|2019–20]]
| {{sortname|John|Robertson|dab=footballer, born 1964}} (3)
|Scotland
| Inverness Caledonian Thistle
|First manager to win the cup three times
|-
| {{sortname|John|McGlynn|dab=Scottish footballer}}
|Scotland
| [[Raith Rovers F.C.|Raith Rovers]]
|
|-
! scope=row style=text-align:center| [[2021–22 Scottish Challenge Cup|2021–22]]
| {{sortname|John|McGlynn|dab=Scottish footballer}} (2)
|Scotland
| [[Raith Rovers F.C.|Raith Rovers]]
|First manager to win the cup two consecutive seasons
|-
! scope=row style=text-align:center| [[2022–23 Scottish Challenge Cup|2022–23]]
| {{sortname|John|Rankin|dab=footballer, born 1983}}
|Scotland
| [[Hamilton Academical  F.C.|Hamilton Academical]]
|
|-
! scope=row style=text-align:center| [[2023–24 Scottish Challenge Cup|2023–24]]
| {{sortname|Rhys|McCabe}}
|Scotland
| [[Airdrieonians F.C.|Airdrieonians]]
|Youngest manager to win the Scottish Challenge Cup, being 31 at the time of the victory.
|-
! scope=row style=text-align:center| [[2024–25 Scottish Challenge Cup|2024–25]]
|{{sortname|David|Martindale}}
|Scotland
|[[Livingston F.C.|Livingston]]
|
|}

== Sponsorship and media coverage ==
[[File:Petrofac.svg|thumb|[[Petrofac]] sponsored the Scottish Challenge Cup from 2014 to 2016.]]
The Scottish Challenge Cup has been [[sponsor (commercial)|sponsored]] several times since it was introduced in [[1990–91 in Scottish football|1990]]. The sponsor has been able to determine the name of the competition. There have been four sponsors since the competition's formation as well as several name changes within the duration of each sponsorship.<ref name="SFL_Final_Results" /> The competition relies on revenue earned from sponsorship although it has been able to run without a sponsor over two periods but had to be suspended for one season in [[1998–99 in Scottish football|1998–99]] as a consequence.<ref name="DAFC_preview" />

* 1990–1995: [[B&Q]] (B&Q Centenary Cup (until 1991) then B&Q Cup)<ref name="DAFC_preview" /><ref name="Fisher_Sunday_Herald_Bells" />
* 1995–1998: No sponsor
* 1999–2006: [[Bell's whisky]] (Bell's Challenge Cup (until 2002) then Bell's Cup)<ref name="DAFC_preview" /><ref name="Fisher_Sunday_Herald_Bells" />
* 2006–2008: No sponsor
* 2008–2011: [[MG Alba]] (ALBA Challenge Cup)<ref>{{cite news|url=http://www.scottishfootballleague.com/news.cfm?curpageid=993&newsid=2430|title=SFL Announces Sponsor of the Challenge Cup.|date=30 July 2008|publisher=Scottish Football League|access-date=11 April 2009}}</ref>
* 2011–2014 Ramsdens (Ramsdens Cup)<ref name="Ramsdens">[http://www.scottishfootballleague.com/news/article/ramsdens-sponsor-the-challenge-cup/ Ramsdens Sponsor the Challenge Cup] {{Webarchive|url=https://web.archive.org/web/20130512184545/http://www.scottishfootballleague.com/news/article/ramsdens-sponsor-the-challenge-cup/ |date=12 May 2013 }}, scottishfootballleague.com. 6 June 2011. Retrieved 29 June 2011.</ref>
* 2014–2016: [[Petrofac]] (Petrofac Training Cup)<ref name="Petrofac">[http://www.spfl.co.uk/news/article/petrofac-training-services-to-sponsor-challenge-cup// Petrofac Training to sponsor Challenge Cup] {{Webarchive|url=https://web.archive.org/web/20151004233759/http://www.spfl.co.uk/news/article/petrofac-training-services-to-sponsor-challenge-cup// |date=4 October 2015 }}, spfl.co.uk. 1 July 2014. Retrieved 1 July 2014.</ref><ref>{{cite web |url=http://www.heraldscotland.com/sport/14544690.Revamped_Challenge_Cup_could_pave_the_way_for_more_cross_border_competitions/ |title=Revamped Challenge Cup could pave the way for more cross-border competitions |publisher=Herald Scotland |first=Graeme |last=Macpherson |date=8 June 2016 |access-date=9 June 2016}}</ref>
* 2016–2019: [[Irn-Bru]] (Irn-Bru Cup)<ref name="Irn-Bru">[http://spfl.co.uk/news/article/irn-bru-adds-fizz-to-challenge-cup/// IRN-BRU adds fizz to Challenge Cup] {{Webarchive|url=https://web.archive.org/web/20160814023821/http://spfl.co.uk/news/article/irn-bru-adds-fizz-to-challenge-cup/// |date=14 August 2016 }}, spfl.co.uk. 9 June 2016. Retrieved 9 June 2016.</ref>
* 2019–2020: [[Tunnock's]] (Tunnock's Caramel Wafer Challenge Cup)<ref>{{cite web |url=https://www.bbc.co.uk/sport/football/48774483 |title=Scottish Challenge Cup: New sponsor a sweet deal |publisher=BBC Sport  |date=26 June 2019}}</ref>
* 2021–2025: SPFL Trust (SPFL Trust Trophy)<ref>{{cite web |url=https://spfltrust.org.uk/spfl-trust-trophy-revealed-new-funds-launch/ |title=SPFL Trust Trophy revealed & new funds launch |website=spfltrust.org |date=15 October 2020 |access-date=15 October 2020}}</ref>
* 2025–: KDM Group (KDM Evolution Trophy)

Selected games have been broadcast live on the [[Scottish Gaelic]] language television channel [[BBC Alba]] since 2008,<ref>{{cite news|url=http://news.bbc.co.uk/sport1/hi/football/scot_div_1/7867162.stm|title=BBC Alba to screen live SFL games|publisher=BBC Sport|date=3 February 2009|access-date=11 April 2009}}</ref> which is run jointly by former sponsor [[MG Alba]] and the [[BBC]].<ref name="BBC_Alba_new">[http://news.bbc.co.uk/sport1/hi/football/scot_cups/7625048.stm BBC Alba to cover Challenge Cup], ''news.bbc.co.uk''. [[BBC Sport]]. 19 September 2008. Retrieved 11 April 2009.</ref> Every final since the [[2008 Scottish Challenge Cup Final|2008 final]] has been broadcast live on the channel<ref name="BBC_Alba_Daily_Record">[http://www.dailyrecord.co.uk/sport/football/sfls-delight-at-joy-sponsorship-deal-985514 SFL's delight at joy sponsorship deal for Challenge Cup] ''dailyrecord.co.uk''. ''[[Daily Record (Scotland)|Daily Record]]''. 31 July 2008. Retrieved 7 April 2013.</ref> and the arrangement was extended for three more years in 2012 despite the end of MG Alba's sponsorship of the competition in 2011.<ref name="BBC_Alba_extend">[https://www.bbc.co.uk/sport/0/football/18982362 BBC ALBA extend Ramsdens Challenge Cup TV deal], ''news.bbc.co.uk''. [[BBC Sport]]. 25 July 2012. Retrieved 7 April 2013.</ref> With the expansion of the competition to include teams from Northern Ireland and Wales from 2016 to 2017, additional contracts for live match coverage have been agreed with [[Premier Sports]] and [[S4C]].<ref name="SPFL Format" />

== See also ==
* [[List of winners of the Scottish League One and predecessors#Scottish League C Division (1946–1955)|Scottish C Division]] League Cup
* Scottish [[B Division Supplementary Cup]]
* [[Spring Cup]]

== References ==
{{Reflist}}

== External links ==
* {{Official website|https://spfl.co.uk/league/challenge-cup}}

{{Scottish Challenge Cup seasons}}
{{Scottish Professional Football League}}
{{Scottish Football League}}
{{Football in Scotland}}

[[Category:Scottish Challenge Cup| ]]
[[Category:Scottish Football League|Challenge Cup]]
[[Category:Scottish Professional Football League|Challenge Cup]]
[[Category:Football cup competitions in Scotland|3]]
[[Category:Recurring sporting events established in 1990]]
[[Category:1990 establishments in Scotland]]