| 1. Round | 17/08/2009 | Dundee United | - | Heart of Midlothian | 2:0 | ||||
| 2. Round | 23/08/2009 | Heart of Midlothian | - | Rangers FC | 1:2 |  |
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| 3. Round | 30/08/2009 | St. Johnstone FC | - | Heart of Midlothian | 2:2 | ||||
| 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 | ||||
| 12. Round | 21/11/2009 | Heart of Midlothian | - | St. Johnstone FC | 1:2 | ||||
| 22. Round | 27/01/2010 | Heart of Midlothian | - | Aberdeen FC | 0:3 |
Italy
