| 1. Round | 09/08/2008 | Heart of Midlothian | - | Motherwell FC | 3:2 |  |
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| 2. Round | 16/08/2008 | Rangers FC | - | Heart of Midlothian | 2:0 |  |
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| 5. Round | 13/09/2008 | Falkirk FC | - | Heart of Midlothian | 2:1 |  |
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| 6. Round | 20/09/2008 | Heart of Midlothian | - | Inverness CT | 1:0 | |
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| 7. Round | 27/09/2008 | Dundee United | - | Heart of Midlothian | 3:0 | ||||
| 8. Round | 04/10/2008 | Heart of Midlothian | - | Kilmarnock FC | 1:2 | ||||
| 10. Round | 25/10/2008 | Heart of Midlothian | - | Aberdeen FC | 1:1 | |
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| 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 | ||||
| 26. Round | 21/02/2009 | Heart of Midlothian | - | St. Mirren FC | 1:1 | ||||
| 28. Round | 04/03/2009 | Heart of Midlothian | - | Motherwell FC | 2:1 | ||||
| 29. Round | 14/03/2009 | Hibernian FC | - | Heart of Midlothian | 1:0 |
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