2. Round | 06/08/2000 | St. Johnstone FC | - | Heart of Midlothian | 2:2 | ||||
3. Round | 13/08/2000 | Aberdeen FC | - | Heart of Midlothian | 1:1 | ||||
5. Round | 19/08/2000 | Heart of Midlothian | - | Celtic FC | 2:4 | ||||
6. Round | 27/08/2000 | Dundee FC | - | Heart of Midlothian | 1:1 | ||||
7. Round | 09/09/2000 | Heart of Midlothian | - | Dunfermline Athletic | 2:0 | ||||
8. Round | 17/09/2000 | Rangers FC | - | Heart of Midlothian | 1:0 | ||||
4. Round | 20/09/2000 | Heart of Midlothian | - | St. Mirren FC | 2:0 | ||||
9. Round | 24/09/2000 | Heart of Midlothian | - | Kilmarnock FC | 0:2 | ||||
10. Round | 01/10/2000 | Heart of Midlothian | - | Motherwell FC | 3:0 | ||||
11. Round | 14/10/2000 | Dundee United | - | Heart of Midlothian | 0:4 | ||||
12. Round | 22/10/2000 | Hibernian FC | - | Heart of Midlothian | 6:2 |