| 13. Round | 28/10/2000 | Heart of Midlothian | - | St. Johnstone FC | 0:3 | ||||
| 15. Round | 11/11/2000 | St. Mirren FC | - | Heart of Midlothian | 1:2 | ||||
| 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 | ||||
| 22. Round | 23/12/2000 | Heart of Midlothian | - | Dundee United | 3:1 | ||||
| 23. Round | 26/12/2000 | Heart of Midlothian | - | Hibernian FC | 1:1 |
Scotland