| 2. Round | 23/08/2009 | Heart of Midlothian | - | Rangers FC | 1:2 | ||||
| 3. Round | 30/08/2009 | St. Johnstone FC | - | Heart of Midlothian | 2:2 | ||||
| 5. Round | 20/09/2009 | Celtic FC | - | Heart of Midlothian | 2:1 | ||||
| 6. Round | 26/09/2009 | Heart of Midlothian | - | Hamilton Academical | 2:1 | ||||
| 7. Round | 03/10/2009 | St. Mirren FC | - | Heart of Midlothian | 2:1 | ||||
| 8. Round | 17/10/2009 | Aberdeen FC | - | Heart of Midlothian | 1:1 | ||||
| 9. Round | 24/10/2009 | Heart of Midlothian | - | Falkirk FC | 0:0 | ||||
| 10. Round | 31/10/2009 | Motherwell FC | - | Heart of Midlothian | 1:0 | ||||
| 11. Round | 07/11/2009 | Heart of Midlothian | - | Hibernian FC | 0:0 | ||||
| 12. Round | 21/11/2009 | Heart of Midlothian | - | St. Johnstone FC | 1:2 | ||||
| 13. Round | 28/11/2009 | Kilmarnock FC | - | Heart of Midlothian | 1:2 | ||||
| 14. Round | 06/12/2009 | Hamilton Academical | - | Heart of Midlothian | 2:1 | ||||
| 27. Round | 27/02/2010 | Aberdeen FC | - | Heart of Midlothian | 0:1 |  |
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| 28. Round | 07/03/2010 | Dundee United | - | Heart of Midlothian | 1:0 | ||||
| 30. Round | 13/03/2010 | Motherwell FC | - | Heart of Midlothian | 3:1 | ||||
| 29. Round | 20/03/2010 | Heart of Midlothian | - | Hibernian FC | 2:1 |
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