| 10. Round | 01/10/2000 | Heart of Midlothian | - | Motherwell FC | 3:0 |  |
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| 11. Round | 14/10/2000 | Dundee United | - | Heart of Midlothian | 0:4 | ||||
| 12. Round | 22/10/2000 | Hibernian FC | - | Heart of Midlothian | 6:2 | ||||
| 13. Round | 28/10/2000 | Heart of Midlothian | - | St. Johnstone FC | 0:3 | ||||
| 16. Round | 18/11/2000 | Celtic FC | - | Heart of Midlothian | 6:1 |  |
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| 17. Round | 25/11/2000 | Heart of Midlothian | - | Dundee FC | 3:1 | |
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| 18. Round | 29/11/2000 | Dunfermline Athletic | - | Heart of Midlothian | 1:0 | ||||
| 19. Round | 03/12/2000 | Heart of Midlothian | - | Rangers FC | 0:1 | ||||
| 20. Round | 09/12/2000 | Kilmarnock FC | - | Heart of Midlothian | 0:3 | ||||
| 21. Round | 16/12/2000 | Motherwell FC | - | Heart of Midlothian | 2:0 | ||||
| 24. Round | 30/12/2000 | St. Johnstone FC | - | Heart of Midlothian | 2:2 | |
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| 25. Round | 02/01/2001 | Aberdeen FC | - | Heart of Midlothian | 1:0 | ||||
| 27. Round | 04/02/2001 | Heart of Midlothian | - | Celtic FC | 0:3 | |
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| 29. Round | 24/02/2001 | Heart of Midlothian | - | Dunfermline Athletic | 7:1 | ||||
| 30. Round | 03/03/2001 | Rangers FC | - | Heart of Midlothian | 2:0 |
Scotland