| 1. Ronde | 09.08.2008 | Heart of Midlothian | - | Motherwell FC | 3:2 |  |
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| 2. Ronde | 16.08.2008 | Rangers FC | - | Heart of Midlothian | 2:0 |  |
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| 5. Ronde | 13.09.2008 | Falkirk FC | - | Heart of Midlothian | 2:1 |  |
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| 6. Ronde | 20.09.2008 | Heart of Midlothian | - | Inverness CT | 1:0 | |
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| 7. Ronde | 27.09.2008 | Dundee United | - | Heart of Midlothian | 3:0 | ||||
| 8. Ronde | 04.10.2008 | Heart of Midlothian | - | Kilmarnock FC | 1:2 | ||||
| 10. Ronde | 25.10.2008 | Heart of Midlothian | - | Aberdeen FC | 1:1 | |
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| 11. Ronde | 02.11.2008 | Heart of Midlothian | - | Celtic FC | 0:2 | ||||
| 12. Ronde | 08.11.2008 | St. Mirren FC | - | Heart of Midlothian | 0:1 | ||||
| 26. Ronde | 21.02.2009 | Heart of Midlothian | - | St. Mirren FC | 1:1 | ||||
| 28. Ronde | 04.03.2009 | Heart of Midlothian | - | Motherwell FC | 2:1 | ||||
| 29. Ronde | 14.03.2009 | Hibernian FC | - | Heart of Midlothian | 1:0 |
Litouwen