1. Round | 11/08/2008 | Hamilton Academical | - | Dundee United | 3:1 | ||||
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 | ||||
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 | ||||
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 |