| 1. Round | 14/08/2010 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 2. Round | 21/08/2010 | Hamilton Academical | - | Heart of Midlothian | 0:4 | ||||
| 3. Round | 29/08/2010 | Heart of Midlothian | - | Dundee United | 1:1 | ||||
| 4. Round | 11/09/2010 | Celtic FC | - | Heart of Midlothian | 3:0 | ||||
| 5. Round | 18/09/2010 | Inverness CT | - | Heart of Midlothian | 1:3 | ||||
| 7. Round | 02/10/2010 | Heart of Midlothian | - | Rangers FC | 1:2 |  |
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| 8. Round | 16/10/2010 | Aberdeen FC | - | Heart of Midlothian | 0:1 | |
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| 9. Round | 23/10/2010 | Heart of Midlothian | - | St. Mirren FC | 3:0 | ||||
| 10. Round | 31/10/2010 | Heart of Midlothian | - | Kilmarnock FC | 0:3 | ||||
| 15. Round | 14/12/2010 | Motherwell FC | - | Heart of Midlothian | 1:2 |
Scotland