2. Round | 17/08/2008 | Dundee United | - | Celtic FC | 1:1 | ||||
3. Round | 23/08/2008 | Motherwell FC | - | Dundee United | 1:1 | ||||
5. Round | 13/09/2008 | Hibernian FC | - | Dundee United | 2:1 | ||||
6. Round | 20/09/2008 | Aberdeen FC | - | Dundee United | 0:1 | ||||
16. Round | 29/11/2008 | St. Mirren FC | - | Dundee United | 0:2 | ||||
17. Round | 06/12/2008 | Inverness CT | - | Dundee United | 1:3 | ||||
18. Round | 13/12/2008 | Dundee United | - | Rangers FC | 2:2 | ||||
19. Round | 20/12/2008 | Heart of Midlothian | - | Dundee United | 0:0 | ||||
24. Round | 31/01/2009 | Rangers FC | - | Dundee United | 2:0 | ||||
25. Round | 14/02/2009 | Dundee United | - | Inverness CT | 1:1 | ||||
26. Round | 21/02/2009 | Aberdeen FC | - | Dundee United | 2:2 | ||||
27. Round | 28/02/2009 | Dundee United | - | Heart of Midlothian | 0:1 | ||||
28. Round | 03/03/2009 | Falkirk FC | - | Dundee United | 0:1 | ||||
29. Round | 14/03/2009 | Motherwell FC | - | Dundee United | 2:1 | ||||
30. Round | 22/03/2009 | Dundee United | - | Celtic FC | 2:2 |