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 | ||||
6. Round | 26/09/2009 | St. Johnstone FC | - | Dundee United | 2:3 | ||||
7. Round | 03/10/2009 | Hibernian FC | - | Dundee United | 1:1 | ||||
14. Round | 05/12/2009 | Dundee United | - | St. Mirren FC | 3:2 | ||||
15. Round | 12/12/2009 | Heart of Midlothian | - | Dundee United | 0:0 | ||||
10. Round | 15/12/2009 | Dundee United | - | Rangers FC | 0:3 |