Challenge Cup winners

1990/91 - 11/11/90 - Fir Park, 11,506
Dundee 3-2 Ayr United (aet)

1991/92 - 08/12/91 - Fir Park, 9,663
Hamilton Accies 1-0 Ayr United

1992/93 - 13/12/92 - Love Street, 7,391
Hamilton Accies 3-2 Morton

1993/94 - 12/12/93 - Fir Park, 13,763
Falkirk 3-0 St Mirren

1994/95 - 06/11/94 - McDiarmid Park, 8,844
Airdrieonians 3-2 Dundee (aet)

1995/96 - 05/11/95 - McDiarmid Park, 7,856
Stenhousemuir 0-0 Dundee United
(aet, Stenhousemuir won 5-4 on penalties)

1996/97 - 03/11/96 - Broadwood, 5,222
Stranraer 1-0 St Johnstone

1997/98 - 02/11/97 - Fir Park, 9,735
Falkirk 1-0 Queen of the South

1998/99 - Competition not held

1999/00 - 21/11/99 - Excelsior Stadium, 4,043
Alloa Athletic 4-4 Inverness CT
(aet, Alloa won 5-4 on penalties)

2000/01 - 19/11/00 - Broadwood, 5,623
Airdrieonians 2-2 Livingston
(aet, Airdrie won 3-2 on penalties)

2001/02 - 14/10/01 - Broadwood, 4,548
Airdrieonians 2-1 Alloa Athletic

2002/03 - 20/10/02 - Broadwood, 6,428
Queen of the South 2-0 Brechin City

2003/04 - 26/10/03 - McDiarmid Park, 5,428
Inverness CT 2-0 Airdrie United

2004/05 - 07/11/04 - McDiarmid Park, 7,471
Falkirk 2-1 Ross County

2005/06 - 06/11/05 - Excelsior Stadium, 9,613
St Mirren 2-1 Hamilton Accies

2006/07 - 12/11/06 - McDiarmid Park, 4,062
Ross County 1-1 Clyde
(Ross County won 5-4 on penalties)

2007/08 - 25/11/07 - Dens Park, 6,446
St Johnstone 3-2 Dunfermline Athletic

2008/09 - 16/11/08 - McDiarmid Park, 4,091
Airdrie United 2-2 Ross County
(aet, Airdrie won 3-2 on penalties)

2009/10 - 22/11/09 - McDiarmid Park, 8,031
Dundee 3-2 Inverness CT

2010/11 - 10/04/11 - McDiarmid Park, 5,214
Ross County 2-0 Queen of the South

2011/12 - 01/04/12 - Almondvale, 5,210
Falkirk 1-0 Hamilton Accies

2012/13 - 07/04/13 - Almondvale, 9,452
Queen of the South 1-1 Partick Thistle
(aet, Queen of the South won 6-5 on penalties)

2013/14 - 06/04/14 - Easter Road, 19,983
Raith Rovers 1-0 Rangers (aet)

2014/15 - 05/04/15 - McDiarmid Park - 2,869
Livingston 4-0 Alloa Athletic

2015/16 - 10/04/16 - Hampden Park - 48,133
Rangers 4-0 Peterhead

2016/17 - 25/03/17 - Fir Park - 8,089
Dundee United 2-1 St Mirren

2017/18 - 24/03/18 - McDiarmid Park - 4,602
Inverness Caledonian Thistle 1-0 Dumbarton

2018/19 - 23/03/19 - Caledonian Stadium - 3,057
Ross County 3-1 Connah's Quay Nomads

2019/20 - 28/03/20 - McDiarmid Park
Raith Rovers v Inverness Caledonian Thistle
Postponed due to Coronavirus pandemic. Clubs subsequently declared joint winners.

2020/21 - Competition not held

2021/22 - 03/04/22 - Excelsior Stadium - 4,452
Raith Rovers 3-1 Queen of the South