The 2004–2005 Scottish Challenge Cup was the 14th season of the competition, competed for by all 30 members of the Scottish Football League. The defending champions were Inverness Caledonian Thistle, who defeated Airdrie United 2–0 in the 2003 final. Inverness Caledonian Thistle did not compete in the tournament after being promoted to the Scottish Premier League.
The 2001–02 Scottish Challenge Cup was the 11th season of the competition, which was also known as the Bell's Challenge Cup for sponsorship reasons. It was competed for by the 30 member clubs of the Scottish Football League. The defending champions were Airdrieonians, who defeated Livingston 3–2 on penalties in the 2000 final.
The 2000–01 Scottish Challenge Cup was the tenth season of the competition, which was also known as the Bell's Challenge Cup for sponsorship reasons. It was competed for by the 30 member clubs of the Scottish Football League. The defending champions were Alloa Athletic, who defeated Inverness Caledonian Thistle 5–4 on penalties in the 1999 final.
The 1999–2000 Scottish Challenge Cup was the ninth season of the competition, which was also known as the Bell's Challenge Cup for sponsorship reasons. It was competed for by the 30 member clubs of the Scottish Football League. The defending champions were Falkirk, who defeated Queen of the South 1–0 in the 1997 final.
The 1997–98 Scottish Challenge Cup was the eighth season of the competition, competed for by the 30 member clubs of the Scottish Football League. The defending champions were Stranraer, who defeated St Johnstone 1–0 in the 1996 final.
The 1996–97 Scottish Challenge Cup was the seventh season of the competition, competed for by the 30 member clubs of the Scottish Football League. The defending champions were Stenhousemuir, who defeated Dundee United 5–4 on penalties after a 0–0 draw after extra time in the 1995 final.
The 2009–10 Scottish League Cup was the 64th season of the Scotland's second most prestigious football knockout competition, also known for sponsorship reasons as the Co-operative Insurance Cup. Rangers won the cup beating St Mirren 1–0 thanks to a goal from Kenny Miller.
The 2009–10 Scottish Challenge Cup, known as the ALBA Challenge Cup due to sponsorship reasons with MG Alba, was the 19th season of the competition, competed for by all 30 members of the Scottish Football League. The previous winner was Airdrie United, who defeated Ross County 3–2 on penalties after a 2–2 draw in the 2008 final. Airdrie United were knocked out in the first round by Partick Thistle after a 1–0 loss.
The 2011–12 Scottish Cup was the 127th season of Scotland's most prestigious football knockout competition. The tournament began on 24 September 2011 and ended on 19 May 2012. It was sponsored by William Hill in the first season of a three-year partnership, known as the William Hill Scottish Cup. The winner of the competition qualified for the play-off round of the 2012–13 UEFA Europa League. Heart of Midlothian won 5–1 against city rivals Hibernian at Hampden Park.
Season 1997–98 saw Livingston compete in the Scottish Second Division. They also competed in the Challenge Cup, League Cup and the Scottish Cup.
The 2013–14 Scottish League Cup was the 68th season of Scotland's second-most prestigious football knockout competition.
The 2015–16 Scottish League Cup was the 70th season of Scotland's second-most prestigious football knockout competition. It is also known as The Scottish League Cup presented by Utilita for sponsorship reasons.
The 2016–17 Scottish League Cup group stage was played from 15 July to 31 July 2016. A total of 40 teams competed in the group stage. The winners of each of the 8 groups, as well as the 4 best runners-up progressed to the second round of the 2016–17 Scottish League Cup.
The 2017–18 Scottish League Cup group stage was played from 14 July to 30 July 2017. A total of 40 teams competed in the group stage. The winners of each of the eight groups, as well as the four best runners-up progressed to the second round of the 2017–18 Scottish League Cup.
The 2018–19 Scottish Challenge Cup, known as the IRN-BRU Cup due to sponsorship reasons, was the 28th season of the competition. The tournament took on a similar format from the previous season with the addition of two teams from England's National League entering the competition for the first time. This took the total number of participating clubs to 58.
The 2018–19 Scottish League Cup group stage was played from 14–28 July 2018. A total of 40 teams competed in the group stage. The winners of each of the eight groups, as well as the four best runners-up progressed to the second round of the 2018–19 Scottish League Cup.
The 2019–20 Scottish League Cup Group stage was played from 12–28 July 2019. A total of 40 teams competed in the group stage. The winners of each of the eight groups, as well as the four best runners-up progressed to the second round of the 2019–20 Scottish League Cup.
The 2020–21 Scottish League Cup Group stage took place from 6 October 2020 to 15 November 2020. A total of 40 teams competed in the group stage. The winners of each of the eight groups, as well as the four best runners-up progressed to the second round of the 2020–21 Scottish League Cup.
The 2021–22 Scottish Challenge Cup known as the SPFL Trust Trophy due to sponsorship reasons, is the 30th season of the competition. The total number of participating clubs is 50, down from 58, with only Scottish clubs competing due to the COVID-19 pandemic in Scotland. The competition began on 10 August 2021 with the First Round and will end on 2 or 3 April 2022 with the final at a yet to be chosen neutral venue.
The 2021–22 Scottish League Cup group stage was played from 10 July 2021 to 25 July 2021. A total of 40 teams competed in the group stage. The winners of each of the eight groups, as well as the three best runners-up progressed to the second round of the 2021–22 Scottish League Cup.