| 1. Round | 30/07/2005 | Dundee United | - | Aberdeen FC | 1:1 | ||||
| 5. Round | 28/08/2005 | Dundee United | - | Inverness CT | 1:1 | ||||
| 6. Round | 10/09/2005 | Hibernian FC | - | Dundee United | 2:1 |  |
|||
| 7. Round | 17/09/2005 | Dundee United | - | Livingston FC | 2:0 | ||||
| 8. Round | 24/09/2005 | Dunfermline Athletic | - | Dundee United | 2:1 | ||||
| 9. Round | 01/10/2005 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
| 10. Round | 16/10/2005 | Dundee United | - | Rangers FC | 0:0 | ||||
| 11. Round | 22/10/2005 | Falkirk FC | - | Dundee United | 1:3 | |
|||
| 12. Round | 25/10/2005 | Aberdeen FC | - | Dundee United | 2:0 | ||||
| 13. Round | 30/10/2005 | Dundee United | - | Celtic FC | 2:4 | ||||
| 14. Round | 05/11/2005 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 15. Round | 19/11/2005 | Dundee United | - | Motherwell FC | 1:1 |  |
|||
| 17. Round | 03/12/2005 | Dundee United | - | Hibernian FC | 1:0 | ||||
| 18. Round | 10/12/2005 | Livingston FC | - | Dundee United | 1:0 | ||||
| 19. Round | 20/12/2005 | Dundee United | - | Dunfermline Athletic | 2:1 | ||||
| 20. Round | 26/12/2005 | Kilmarnock FC | - | Dundee United | 2:1 | ||||
| 21. Round | 31/12/2005 | Rangers FC | - | Dundee United | 3:0 | ||||
| 22. Round | 15/01/2006 | Dundee United | - | Falkirk FC | 2:1 |
Scotland