4. Round | 30/08/2008 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
5. Round | 13/09/2008 | Hibernian FC | - | Dundee United | 2:1 | ||||
6. Round | 20/09/2008 | Aberdeen FC | - | Dundee United | 0:1 | ||||
9. Round | 04/11/2008 | Rangers FC | - | Dundee United | 3:3 | ||||
12. Round | 08/11/2008 | Dundee United | - | Aberdeen FC | 2:1 | ||||
13. Round | 12/11/2008 | Dundee United | - | Hibernian FC | 2:0 | ||||
15. Round | 22/11/2008 | Dundee United | - | Hamilton Academical | 1:1 | ||||
24. Round | 31/01/2009 | Rangers FC | - | Dundee United | 2:0 | ||||
31. Round | 04/04/2009 | Dundee United | - | Hibernian FC | 2:2 | ||||
32. Round | 11/04/2009 | Hamilton Academical | - | Dundee United | 0:1 | ||||
33. Round | 18/04/2009 | Dundee United | - | Kilmarnock FC | 0:0 |