| 1. Jornada | 31.07.1999 | Dundee United | - | Dundee FC | 2:1 | ||||
| 2. Jornada | 07.08.1999 | Motherwell FC | - | Dundee United | 2:2 |  |
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| 3. Jornada | 15.08.1999 | Dundee United | - | Celtic FC | 2:1 | ||||
| 4. Jornada | 21.08.1999 | Rangers FC | - | Dundee United | 4:1 | ||||
| 5. Jornada | 29.08.1999 | Dundee United | - | Kilmarnock FC | 0:0 | |
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| 7. Jornada | 18.09.1999 | Aberdeen FC | - | Dundee United | 1:2 | ||||
| 8. Jornada | 25.09.1999 | Dundee United | - | Heart of Midlothian | 0:2 | ||||
| 20. Jornada | 27.12.1999 | Aberdeen FC | - | Dundee United | 3:1 | ||||
| 21. Jornada | 22.01.2000 | Dundee United | - | Hibernian FC | 0:0 | ||||
| 15. Jornada | 02.02.2000 | Dundee United | - | Rangers FC | 0:4 | |
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| 25. Jornada | 04.03.2000 | Dundee United | - | Heart of Midlothian | 0:1 | ||||
| 22. Jornada | 15.03.2000 | Dundee United | - | Kilmarnock FC | 2:2 | ||||
| 23. Jornada | 04.04.2000 | Rangers FC | - | Dundee United | 3:0 | ||||
| 30. Jornada | 08.04.2000 | Kilmarnock FC | - | Dundee United | 1:0 |
Islandia