| 4. Jornada | 21.08.1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
| 5. Jornada | 29.08.1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
| 6. Jornada | 12.09.1999 | Kilmarnock FC | - | Celtic FC | 0:1 |  |
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| 7. Jornada | 19.09.1999 | Hibernian FC | - | Kilmarnock FC | 0:3 | ||||
| 8. Jornada | 25.09.1999 | Kilmarnock FC | - | Dundee FC | 0:2 | |
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| 10. Jornada | 16.10.1999 | Kilmarnock FC | - | Rangers FC | 1:1 | ||||
| 11. Jornada | 23.10.1999 | Aberdeen FC | - | Kilmarnock FC | 2:2 | |
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| 9. Jornada | 27.10.1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 | ||||
| 12. Jornada | 30.10.1999 | Celtic FC | - | Kilmarnock FC | 5:1 |  |
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| 21. Jornada | 23.01.2000 | Kilmarnock FC | - | Celtic FC | 1:1 | ||||
| 17. Jornada | 26.01.2000 | Dundee FC | - | Kilmarnock FC | 0:0 |
Escocia