1. Round | 09/08/2008 | Heart of Midlothian | - | Motherwell FC | 3:2 | ||||
2. Round | 16/08/2008 | Rangers FC | - | Heart of Midlothian | 2:0 | ||||
3. Round | 23/08/2008 | Heart of Midlothian | - | St. Mirren FC | 2:1 | ||||
10. Round | 25/10/2008 | Heart of Midlothian | - | Aberdeen FC | 1:1 | ||||
11. Round | 02/11/2008 | Heart of Midlothian | - | Celtic FC | 0:2 | ||||
16. Round | 29/11/2008 | Heart of Midlothian | - | Rangers FC | 2:1 | ||||
18. Round | 13/12/2008 | Celtic FC | - | Heart of Midlothian | 1:1 | ||||
19. Round | 20/12/2008 | Heart of Midlothian | - | Dundee United | 0:0 | ||||
21. Round | 03/01/2009 | Heart of Midlothian | - | Hibernian FC | 0:0 | ||||
17. Round | 07/01/2009 | Motherwell FC | - | Heart of Midlothian | 1:0 | ||||
22. Round | 17/01/2009 | Kilmarnock FC | - | Heart of Midlothian | 0:2 | ||||
27. Round | 28/02/2009 | Dundee United | - | Heart of Midlothian | 0:1 | ||||
30. Round | 21/03/2009 | Rangers FC | - | Heart of Midlothian | 2:2 |