Honours Summary
| Wins | Teams |
| 3 | Airdrieonians, Falkirk |
| 2 | Hamilton Academical |
| 1 | Airdrie United, Alloa Athletic, Dundee, Inverness CT, Queen of the South, Ross County, St Johnstone, St Mirren, Stenhousemuir, Stranraer |
Past Seasons
| Season | Final details, if applicable |
| Scottish Challenge Cup | |
| 2008-2009 | Airdrie United 2 Ross County 2, aet, Airdrie Utd won on penalties |
| 2007-2008 | St Johnstone 3 Dunfermline Athletic 2 |
| 2006-2007 | Ross County 1 Clyde 1, aet, Ross Co won on penalties |
| 2005-2006 | St Mirren 2 Hamilton Academical 1 |
| 2004-2005 | Falkirk 2 Ross County 1 |
| 2003-2004 | Inverness CT 2 Airdrie United 0 |
| 2002-2003 | Queen of the South 2 Brechin City 0 |
| 2001-2002 | Airdrieonians 2 Alloa Athletic 1 |
| 2000-2001 | Airdrieonians 2 Livingston 2, aet, Airdrieonians won on penalties |
| 1999-2000 | Alloa Athletic 4 Inverness CT 4, aet, Alloa Ath won on penalties |
| 1997-1998 | Falkirk 1 Queen of the South 0 |
| 1996-1997 | Stranraer 1 St Johnstone 0 |
| 1995-1996 | Stenhousemuir 0 Dundee United 0, aet, Stenhousemuir won on penalties |
| 1994-1995 | Airdrieonians 3 Dundee 2, aet |
| 1993-1994 | Falkirk 3 St Mirren 0 |
| 1992-1993 | Hamilton Academical 3 Morton 2 |
| 1991-1992 | Hamilton Academical 1 Ayr United 0 |
| 1990-1991 | Dundee 3 Ayr United 2, aet |
