| 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 | ||||
| 15. Round | 12/12/2009 | Heart of Midlothian | - | Dundee United | 0:0 | ||||
| 16. Round | 20/12/2009 | Heart of Midlothian | - | Celtic FC | 2:1 | ||||
| 17. Round | 26/12/2009 | Falkirk FC | - | Heart of Midlothian | 0:1 | ||||
| 18. Round | 30/12/2009 | Heart of Midlothian | - | Motherwell FC | 1:0 | ||||
| 20. Round | 16/01/2010 | Heart of Midlothian | - | St. Mirren FC | 1:0 | ||||
| 21. Round | 23/01/2010 | Rangers FC | - | Heart of Midlothian | 1:1 |  |
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| 22. Round | 27/01/2010 | Heart of Midlothian | - | Aberdeen FC | 0:3 | ||||
| 31. Round | 27/03/2010 | Heart of Midlothian | - | Rangers FC | 1:4 | ||||
| 33. Round | 10/04/2010 | Heart of Midlothian | - | Kilmarnock FC | 1:0 |
Scotland