| 5. Ronde | 29.08.1999 | Aberdeen FC | - | St. Johnstone FC | 0:3 | ||||
| 7. Ronde | 18.09.1999 | Aberdeen FC | - | Dundee United | 1:2 | ||||
| 9. Ronde | 02.10.1999 | Aberdeen FC | - | Hibernian FC | 2:2 | ||||
| 10. Ronde | 16.10.1999 | Celtic FC | - | Aberdeen FC | 7:0 | ||||
| 8. Ronde | 20.10.1999 | Motherwell FC | - | Aberdeen FC | 5:6 | ||||
| 11. Ronde | 23.10.1999 | Aberdeen FC | - | Kilmarnock FC | 2:2 | ||||
| 12. Ronde | 30.10.1999 | Aberdeen FC | - | Rangers FC | 1:5 | ||||
| 16. Ronde | 27.11.1999 | Hibernian FC | - | Aberdeen FC | 2:0 |  |
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| 15. Ronde | 08.12.1999 | Aberdeen FC | - | Heart of Midlothian | 3:1 | ||||
| 18. Ronde | 11.12.1999 | Aberdeen FC | - | Celtic FC | 0:6 | ||||
| 20. Ronde | 27.12.1999 | Aberdeen FC | - | Dundee United | 3:1 | |
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| 21. Ronde | 22.01.2000 | Rangers FC | - | Aberdeen FC | 5:0 | |
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| 22. Ronde | 05.02.2000 | Aberdeen FC | - | St. Johnstone FC | 2:1 | ||||
| 25. Ronde | 04.03.2000 | Motherwell FC | - | Aberdeen FC | 1:0 | |
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| 27. Ronde | 18.04.2000 | Aberdeen FC | - | Dundee FC | 0:1 | |
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| 32. Ronde | 22.04.2000 | Aberdeen FC | - | Motherwell FC | 2:1 | ||||
| 30. Ronde | 02.05.2000 | St. Johnstone FC | - | Aberdeen FC | 2:1 | ||||
| 34. Ronde | 06.05.2000 | Celtic FC | - | Aberdeen FC | 5:1 |
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