| 1. Jornada | 09.08.2008 | Heart of Midlothian | - | Motherwell FC | 3:2 |  |
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| 2. Jornada | 16.08.2008 | Rangers FC | - | Heart of Midlothian | 2:0 | ||||
| 3. Jornada | 23.08.2008 | Heart of Midlothian | - | St. Mirren FC | 2:1 | ||||
| 4. Jornada | 30.08.2008 | Hamilton Academical | - | Heart of Midlothian | 1:2 | ||||
| 5. Jornada | 13.09.2008 | Falkirk FC | - | Heart of Midlothian | 2:1 | ||||
| 6. Jornada | 20.09.2008 | Heart of Midlothian | - | Inverness CT | 1:0 | |
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| 7. Jornada | 27.09.2008 | Dundee United | - | Heart of Midlothian | 3:0 | ||||
| 8. Jornada | 04.10.2008 | Heart of Midlothian | - | Kilmarnock FC | 1:2 | ||||
| 10. Jornada | 25.10.2008 | Heart of Midlothian | - | Aberdeen FC | 1:1 |
Rusia