2. Round | 17/08/2008 | Dundee United | - | Celtic FC | 1:1 | ||||
12. Round | 08/11/2008 | Dundee United | - | Aberdeen FC | 2:1 | ||||
15. Round | 22/11/2008 | Dundee United | - | Hamilton Academical | 1:1 | ||||
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 | ||||
22. Round | 18/01/2009 | Dundee United | - | Motherwell FC | 0:4 | ||||
23. Round | 24/01/2009 | Dundee United | - | St. Mirren FC | 3:2 | ||||
24. Round | 31/01/2009 | Rangers FC | - | Dundee United | 2:0 | ||||
26. Round | 21/02/2009 | Aberdeen FC | - | Dundee United | 2:2 | ||||
28. Round | 03/03/2009 | Falkirk FC | - | Dundee United | 0:1 | ||||
30. Round | 22/03/2009 | Dundee United | - | Celtic FC | 2:2 | ||||
32. Round | 11/04/2009 | Hamilton Academical | - | Dundee United | 0:1 |