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 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 Cup was the 125th season of Scotland's most prestigious football knockout competition. The competition was sponsored by the Scottish Government and for sponsorship reasons was known as the Active Nation Scottish Cup.
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 2009–10 season was the 100th season of competitive football by Ayr United.
The 2011–12 Scottish League Cup was the 66th season of Scotland's second-most prestigious football knockout competition, the Scottish League Cup, also known as the Scottish Communities League Cup for sponsorship reasons. It was won by Kilmarnock
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 2003–04 season was Motherwell's 6th season in the Scottish Premier League, and their 19th consecutive season in the top division of Scottish football.
Season 1998-99 saw Livingston compete in the Scottish Second Division. They also competed in the League Cup and the Scottish Cup.
The 2009–10 season was Dundee's 5th consecutive season in the Scottish First Division following their relegation from the SPL in 2005. Dundee finished as runners-up in the league, losing out to Inverness Caledonian Thistle. The Dee reached the quarter-finals in both the Scottish Cup & Scottish League Cup and were winners of the Challenge Cup for the second time in the club's history and first since 1991.
The 2012–13 Scottish Cup was the 128th season of Scotland's most prestigious football knockout competition. The tournament began on 4 August 2012 and ended on 26 May 2013. It was sponsored by bookmaker William Hill in the second season of a three-year partnership and is known as the William Hill Scottish Cup. The winner of the competition qualified for the third qualifying round of the 2013–14 UEFA Europa League. The holders Hearts were knocked out by their Edinburgh rivals Hibernian in the fourth round, in a repeat of the previous season's final.
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 League Cup was the 69th season of Scotland's second-most prestigious football knockout competition. It is also known as The Scottish League Cup presented by QTS for sponsorship reasons.
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 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 2018–19Inverness Caledonian Thistle F.C. season is the club's second season in the Scottish Championship, having been relegated from the Scottish Premiership at the end of the 2016–17 season. Caley Thistle will also compete in the Scottish Challenge Cup, Scottish League Cup and the Scottish Cup. This season will be the 25th season since Inverness joined the Scottish Football League. This season is also the return of the Highland derby after Ross County were relegated one season after Inverness.
The 2021–22 season was Raith Rovers' second season back in the second tier of Scottish football after being promoted from Scottish League One at the end of the 2019–20 season. Raith Rovers also competed in the League Cup, Challenge Cup & the Scottish Cup.
