| 3. Round | 13/08/2000 | Aberdeen FC | - | Heart of Midlothian | 1:1 | ||||
| 6. Round | 27/08/2000 | Dundee FC | - | Heart of Midlothian | 1:1 | ||||
| 9. Round | 24/09/2000 | Heart of Midlothian | - | Kilmarnock FC | 0:2 |  |
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| 13. Round | 28/10/2000 | Heart of Midlothian | - | St. Johnstone FC | 0:3 | ||||
| 14. Round | 04/11/2000 | Heart of Midlothian | - | Aberdeen FC | 3:0 | ||||
| 15. Round | 11/11/2000 | St. Mirren FC | - | Heart of Midlothian | 1:2 | |
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| 16. Round | 18/11/2000 | Celtic FC | - | Heart of Midlothian | 6:1 | |
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| 18. Round | 29/11/2000 | Dunfermline Athletic | - | Heart of Midlothian | 1:0 | ||||
| 20. Round | 09/12/2000 | Kilmarnock FC | - | Heart of Midlothian | 0:3 | ||||
| 21. Round | 16/12/2000 | Motherwell FC | - | Heart of Midlothian | 2:0 | ||||
| 23. Round | 26/12/2000 | Heart of Midlothian | - | Hibernian FC | 1:1 | |
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| 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 |
Scotland
