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 | ||||
4. Round | 30/08/2008 | Hamilton Academical | - | Heart of Midlothian | 1:2 | ||||
5. Round | 13/09/2008 | Falkirk FC | - | Heart of Midlothian | 2:1 | ||||
6. Round | 20/09/2008 | Heart of Midlothian | - | Inverness CT | 1:0 | ||||
7. Round | 27/09/2008 | Dundee United | - | Heart of Midlothian | 3:0 | ||||
8. Round | 04/10/2008 | Heart of Midlothian | - | Kilmarnock FC | 1:2 | ||||
9. Round | 19/10/2008 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
10. Round | 25/10/2008 | Heart of Midlothian | - | Aberdeen FC | 1:1 | ||||
11. Round | 02/11/2008 | Heart of Midlothian | - | Celtic FC | 0:2 | ||||
12. Round | 08/11/2008 | St. Mirren FC | - | Heart of Midlothian | 0:1 | ||||
13. Round | 12/11/2008 | Heart of Midlothian | - | Hamilton Academical | 1:0 | ||||
18. Round | 13/12/2008 | Celtic FC | - | Heart of Midlothian | 1:1 |