1. Round | 17/08/2009 | Dundee United | - | Heart of Midlothian | 2:0 | ||||
2. Round | 22/08/2009 | St. Mirren FC | - | Dundee United | 0:0 | ||||
3. Round | 29/08/2009 | Dundee United | - | Falkirk FC | 2:1 | ||||
4. Round | 12/09/2009 | Celtic FC | - | Dundee United | 1:1 | ||||
5. Round | 19/09/2009 | Dundee United | - | Motherwell FC | 0:1 | ||||
6. Round | 26/09/2009 | St. Johnstone FC | - | Dundee United | 2:3 | ||||
7. Round | 03/10/2009 | Hibernian FC | - | Dundee United | 1:1 | ||||
9. Round | 24/10/2009 | Aberdeen FC | - | Dundee United | 0:2 | ||||
11. Round | 07/11/2009 | Kilmarnock FC | - | Dundee United | 0:2 | ||||
12. Round | 22/11/2009 | Dundee United | - | Celtic FC | 2:1 | ||||
13. Round | 28/11/2009 | Motherwell FC | - | Dundee United | 2:2 | ||||
15. Round | 12/12/2009 | Heart of Midlothian | - | Dundee United | 0:0 | ||||
10. Round | 15/12/2009 | Dundee United | - | Rangers FC | 0:3 | ||||
17. Round | 26/12/2009 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
18. Round | 30/12/2009 | Rangers FC | - | Dundee United | 7:1 | ||||
19. Round | 02/01/2010 | Dundee United | - | Aberdeen FC | 0:1 | ||||
32. Round | 05/04/2010 | St. Johnstone FC | - | Dundee United | 0:1 | ||||
33. Round | 14/04/2010 | Dundee United | - | Rangers FC | 0:0 |