| 5. Round | 13/09/2008 | Falkirk FC | - | Heart of Midlothian | 2:1 | ||||
| 6. Round | 20/09/2008 | Heart of Midlothian | - | Inverness CT | 1:0 | ||||
| 25. Round | 14/02/2009 | Heart of Midlothian | - | Aberdeen FC | 2:1 | ||||
| 27. Round | 28/02/2009 | Dundee United | - | Heart of Midlothian | 0:1 | ||||
| 28. Round | 04/03/2009 | Heart of Midlothian | - | Motherwell FC | 2:1 |  |
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| 29. Round | 14/03/2009 | Hibernian FC | - | Heart of Midlothian | 1:0 | ||||
| 33. Round | 18/04/2009 | Falkirk FC | - | Heart of Midlothian | 0:0 |
Poland