Cup Winners
| Stagione | Club | |
| 2013/2014 |  | Raith Rovers |
| 2012/2013 |  | Queen of the South |
| 2011/2012 |  | Falkirk |
| 2010/2011 |  | Ross County |
| 2009/2010 |  | Dundee |
| 2008/2009 |  | Airdrieonians |
| 2007/2008 |  | St. Johnstone |
| 2006/2007 | | Ross County |
| 2005/2006 |  | St. Mirren |
| 2004/2005 | | Falkirk |
| 2003/2004 |  | Inverness CT |
| 2002/2003 | | Queen of the South |
| 2001/2002 | | Airdrieonians |
| 2000/2001 | | Airdrieonians |
| 1999/2000 |  | Alloa Athletic |
| 1997/1998 | | Falkirk |
| 1996/1997 |  | Stranraer |
| 1995/1996 |  | Stenhousemuir |
| 1994/1995 | | Airdrieonians |
| 1993/1994 | | Falkirk |
| 1992/1993 |  | Hamilton Academical |
| 1991/1992 | | Hamilton Academical |
| 1990/1991 | | Dundee |