| 1. Ronde | 31.07.1999 | Dundee United | - | Dundee FC | 2:1 | ||||
| 2. Ronde | 07.08.1999 | Motherwell FC | - | Dundee United | 2:2 |  |
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| 3. Ronde | 15.08.1999 | Dundee United | - | Celtic FC | 2:1 | |
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| 4. Ronde | 21.08.1999 | Rangers FC | - | Dundee United | 4:1 | ||||
| 5. Ronde | 29.08.1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
| 6. Ronde | 11.09.1999 | Dundee United | - | Hibernian FC | 3:1 | |
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| 7. Ronde | 18.09.1999 | Aberdeen FC | - | Dundee United | 1:2 | |
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| 8. Ronde | 25.09.1999 | Dundee United | - | Heart of Midlothian | 0:2 | ||||
| 10. Ronde | 17.10.1999 | Dundee FC | - | Dundee United | 0:2 | |
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| 11. Ronde | 23.10.1999 | Dundee United | - | Motherwell FC | 0:2 | ||||
| 9. Ronde | 27.10.1999 | St. Johnstone FC | - | Dundee United | 0:1 | |
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| 12. Ronde | 31.10.1999 | Hibernian FC | - | Dundee United | 3:2 | |
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| 13. Ronde | 06.11.1999 | Dundee United | - | Aberdeen FC | 3:1 | |
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| 14. Ronde | 20.11.1999 | Kilmarnock FC | - | Dundee United | 1:1 | ||||
| 16. Ronde | 27.11.1999 | Dundee United | - | St. Johnstone FC | 1:0 |
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