| 1. Round | 30/07/1999 | Dundee United | - | Dundee FC | 2:1 | ||||
| 2. Round | 06/08/1999 | Motherwell FC | - | Dundee United | 2:2 |  |
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| 3. Round | 14/08/1999 | Dundee United | - | Celtic FC | 2:1 | ||||
| 4. Round | 20/08/1999 | Rangers FC | - | Dundee United | 4:1 | ||||
| 5. Round | 28/08/1999 | Dundee United | - | Kilmarnock FC | 0:0 | |
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| 7. Round | 17/09/1999 | Aberdeen FC | - | Dundee United | 1:2 | ||||
| 8. Round | 24/09/1999 | Dundee United | - | Heart of Midlothian | 0:2 | ||||
| 20. Round | 26/12/1999 | Aberdeen FC | - | Dundee United | 3:1 | ||||
| 21. Round | 21/01/2000 | Dundee United | - | Hibernian FC | 0:0 | ||||
| 15. Round | 01/02/2000 | Dundee United | - | Rangers FC | 0:4 | |
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| 25. Round | 03/03/2000 | Dundee United | - | Heart of Midlothian | 0:1 | ||||
| 22. Round | 14/03/2000 | Dundee United | - | Kilmarnock FC | 2:2 | ||||
| 23. Round | 03/04/2000 | Rangers FC | - | Dundee United | 3:0 | ||||
| 30. Round | 07/04/2000 | Kilmarnock FC | - | Dundee United | 1:0 |
Iceland