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 2010–11 Scottish Challenge Cup, known as the ALBA Challenge Cup due to sponsorship reasons with MG Alba, was the 20th season of the competition, competed for by all 30 members of the Scottish Football League. The defending champions were Dundee, who defeated Inverness Caledonian Thistle 3–2 in the 2009 final. Dundee were knocked out in the second round after being defeated 4–1 by Stenhousemuir.
The 2011–12 Scottish Challenge Cup, known as the Ramsdens Challenge Cup due to sponsorship reasons with Ramsdens, was the 21st season of the competition. It was competed for by 32 clubs, which included the 30 members of the Scottish Football League, and for the first time the top two clubs of the Highland Football League.
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.
The 2011–12 season was Dumbarton's third consecutive season in the Scottish Second Division, having been promoted from the Scottish Third Division at the end of the 2008–09 season. Dumbarton also competed in the Challenge Cup, League Cup and Scottish Cup.
The 2011–12 season saw Cowdenbeath play their first season back in the Scottish Second Division, having been relegated from the Scottish First Division at the end of the 2010–11 season. Cowdenbeath also competed in the Challenge Cup, League Cup and the Scottish Cup.
The 2011–12 season was Forfar Athletic's second consecutive season in the Scottish Second Division, having been promoted from the Scottish Third Division at the end of the 2009–10 season. Forfar Athletic also competed in the Challenge Cup, League Cup and the Scottish Cup.
Season 1998–99 saw Livingston compete in the Scottish Second Division. They also competed in the League Cup and the Scottish Cup.
The 2012–13 Scottish Challenge Cup, known as the Ramsdens Challenge Cup due to sponsorship reasons with Ramsdens, was the 22nd season of the competition. It was competed for by 32 clubs, which included the 30 members of the 2012–13 Scottish Football League, and for the second season running, the top two Highland Football League clubs with a valid SFA club licence.
The 2010–11 season was Dumbarton's second consecutive season in the Scottish Second Division, having been promoted from the Scottish Third Division at the end of the 2008–09 season. Dumbarton also competed in the Challenge Cup, League Cup and the Scottish Cup.
The 2013–14 Scottish Challenge Cup, known as the Ramsdens Challenge Cup due to sponsorship reasons with Ramsdens, was the 23rd season of the competition. It was contested by 32 clubs, which included the 30 members of the 2013–14 Scottish Championship-League Two, the top Highland League club with a valid SFA club licence and the winner of a preliminary round tie between the highest placed top in the East of Scotland League with a valid SFA club licence (Spartans) and their counterparts in the South of Scotland League, the preliminary tie was a two-legged tie played on the Saturdays of 13 and 20 July with Spartans at home in the 1st leg. Spartans came out on top.
The 2013–14 Scottish League Cup was the 68th season of Scotland's second-most prestigious football knockout competition.
The 2013–14 Scottish Cup was the 129th season of Scotland's most prestigious football knockout competition. The tournament began on 14 September 2013 and ended on 17 May 2014. It was sponsored by bookmaker William Hill in the third season of a five-year partnership after a two-year extension was agreed, and was known as the William Hill Scottish Cup. The winner of the competition qualified for the second qualifying round of the 2014–15 UEFA Europa League.
The 2014–15 Scottish Challenge Cup, known as the Petrofac Training Cup due to sponsorship reasons with Petrofac, was the 24th season of the competition. It was competed for by 32 clubs, which included the 30 members of the 2014–15 Scottish Championship-League Two, the top Highland League club with a valid SFA club licence and the highest placed team from the previous season in the Lowland League with a valid SFA club licence (Spartans).
The 2015–16 Scottish Cup was the 131st season of Scotland's most prestigious football knockout competition. The tournament was sponsored by bookmaker William Hill in what was the fifth season of a five-year partnership. The final was contested between second-tier clubs for the first time ever with no Premiership clubs reaching the final.
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 2015–16 Scottish Challenge Cup, known as the Petrofac Training Cup due to sponsorship reasons, was the 25th season of the competition. It was competed for by 32 clubs, which include the 30 members of the 2015–16 Scottish Championship, 2015–16 Scottish League One and 2015–16 Scottish League Two, the top 2014–15 Highland Football League club with a valid SFA club licence and the highest placed team from the 2014–15 Lowland Football League with a valid SFA club licence.
The 2017–18 Scottish Challenge Cup, known as the IRN-BRU Cup due to sponsorship reasons, is the 27th season of the competition. The tournament took on a similar format from the previous season, however, two teams from the Republic of Ireland's Airtricity League entered the competition for the first time taking the total number of participating clubs to 56. This was the second season with two clubs from both Northern Ireland and Wales competing alongside the 30 members of the 2017–18 Scottish Championship, 2017–18 Scottish League One and 2017–18 Scottish League Two, four teams from the 2017–18 Highland Football League and four from the 2017–18 Lowland Football League as well as the Under-20 teams of the teams competing in the 2017–18 Scottish Premiership. The Welsh teams were The New Saints and Connah's Quay Nomads while the Northern Irish teams were Crusaders and Linfield.
The 2022–23 season will be Dumbarton Football Club's first in Scottish League Two, the fourth tier of Scottish football, having finished ninth in the division in 2021–22 season and been relegated via the playoffs. Dumbarton will also compete in the Scottish League Cup and the Scottish Cup.
