1. Round | 11/08/2008 | Hamilton Academical | - | Dundee United | 3:1 | ||||
4. Round | 30/08/2008 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
6. Round | 20/09/2008 | Aberdeen FC | - | Dundee United | 0:1 | ||||
7. Round | 27/09/2008 | Dundee United | - | Heart of Midlothian | 3:0 | ||||
8. Round | 04/10/2008 | Dundee United | - | Inverness CT | 2:1 | ||||
10. Round | 25/10/2008 | Dundee United | - | St. Mirren FC | 2:0 | ||||
11. Round | 01/11/2008 | Falkirk FC | - | Dundee United | 0:0 | ||||
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 | ||||
14. Round | 15/11/2008 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
15. Round | 22/11/2008 | Dundee United | - | Hamilton Academical | 1:1 | ||||
20. Round | 27/12/2008 | Dundee United | - | Falkirk FC | 1:0 | ||||
21. Round | 03/01/2009 | Celtic FC | - | Dundee United | 2:2 | ||||
22. Round | 18/01/2009 | Dundee United | - | Motherwell FC | 0:4 | ||||
23. Round | 24/01/2009 | Dundee United | - | St. Mirren FC | 3:2 | ||||
31. Round | 04/04/2009 | Dundee United | - | Hibernian FC | 2:2 |