| 1. Round | 30/07/2000 | Dundee United | - | Celtic FC | 1:2 | ||||
| 3. Round | 12/08/2000 | Dundee United | - | Motherwell FC | 1:1 | ||||
| 6. Round | 26/08/2000 | Dunfermline Athletic | - | Dundee United | 1:0 | ||||
| 9. Round | 23/09/2000 | Dundee United | - | Aberdeen FC | 3:5 |  |
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| 15. Round | 11/11/2000 | Dundee United | - | Dundee FC | 0:2 | ||||
| 16. Round | 18/11/2000 | St. Johnstone FC | - | Dundee United | 1:0 | ||||
| 17. Round | 25/11/2000 | Dundee United | - | Dunfermline Athletic | 3:2 | ||||
| 18. Round | 28/11/2000 | Dundee United | - | Kilmarnock FC | 0:1 | ||||
| 19. Round | 05/12/2000 | St. Mirren FC | - | Dundee United | 1:1 | ||||
| 21. Round | 17/12/2000 | Dundee United | - | Rangers FC | 1:1 |
Scotland