| 16. Round | 20/12/2009 | Heart of Midlothian | - | Celtic FC | 2:1 |  |
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| 17. Round | 26/12/2009 | Falkirk FC | - | Heart of Midlothian | 0:1 | ||||
| 18. Round | 30/12/2009 | Heart of Midlothian | - | Motherwell FC | 1:0 | ||||
| 19. Round | 03/01/2010 | Hibernian FC | - | Heart of Midlothian | 1:1 | |
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| 20. Round | 16/01/2010 | Heart of Midlothian | - | St. Mirren FC | 1:0 | ||||
| 26. Round | 21/02/2010 | Heart of Midlothian | - | Hamilton Academical | 2:0 |  |
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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 | |
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| 31. Round | 27/03/2010 | Heart of Midlothian | - | Rangers FC | 1:4 | ||||
| 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 |
Scotland