| 4. Round | 15/09/2009 | Heart of Midlothian | - | Kilmarnock FC | 1:0 |  |
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| 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 | |
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| 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 |  |
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| 23. Round | 30/01/2010 | St. Johnstone FC | - | Heart of Midlothian | 1:0 | ||||
| 29. Round | 20/03/2010 | Heart of Midlothian | - | Hibernian FC | 2:1 | |
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| 32. Round | 03/04/2010 | St. Mirren FC | - | Heart of Midlothian | 1:1 | ||||
| 33. Round | 10/04/2010 | Heart of Midlothian | - | Kilmarnock FC | 1:0 |
England
