| 6. Jornada | 12.09.1999 | Kilmarnock FC | - | Celtic FC | 0:1 | ||||
| 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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| 14. Jornada | 20.11.1999 | Kilmarnock FC | - | Dundee United | 1:1 | ||||
| 16. Jornada | 27.11.1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 | ||||
| 18. Jornada | 11.12.1999 | Rangers FC | - | Kilmarnock FC | 1:0 | ||||
| 23. Jornada | 12.02.2000 | Kilmarnock FC | - | Motherwell FC | 0:2 | ||||
| 32. Jornada | 22.04.2000 | Dundee FC | - | Kilmarnock FC | 1:2 | ||||
| 34. Jornada | 07.05.2000 | Kilmarnock FC | - | Rangers FC | 0:2 |
Escocia