| 22. Round | 04/02/2000 | Celtic FC | - | Heart of Midlothian | 2:3 | ||||
| 24. Round | 25/02/2000 | Heart of Midlothian | - | Kilmarnock FC | 0:0 | ||||
| 20. Round | 29/02/2000 | Motherwell FC | - | Heart of Midlothian | 0:2 | ||||
| 25. Round | 03/03/2000 | Dundee United | - | Heart of Midlothian | 0:1 | ||||
| 18. Round | 14/03/2000 | St. Johnstone FC | - | Heart of Midlothian | 0:1 | ||||
| 27. Round | 17/03/2000 | Hibernian FC | - | Heart of Midlothian | 3:1 |  |
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| 30. Round | 07/04/2000 | Heart of Midlothian | - | Celtic FC | 1:0 | ||||
| 26. Round | 11/04/2000 | Heart of Midlothian | - | Rangers FC | 1:2 | ||||
| 31. Round | 14/04/2000 | Aberdeen FC | - | Heart of Midlothian | 1:2 | ||||
| 32. Round | 21/04/2000 | Heart of Midlothian | - | Dundee United | 1:2 | ||||
| 33. Round | 28/04/2000 | Kilmarnock FC | - | Heart of Midlothian | 0:1 | |
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| 34. Round | 05/05/2000 | Heart of Midlothian | - | St. Johnstone FC | 0:0 | ||||
| 35. Round | 12/05/2000 | Rangers FC | - | Heart of Midlothian | 1:0 | ||||
| 36. Round | 20/05/2000 | Heart of Midlothian | - | Hibernian FC | 2:1 |
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