| 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 | ||||
| 7. Jornada | 19.09.1999 | Hibernian FC | - | Kilmarnock FC | 0:3 |  |
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| 8. Jornada | 25.09.1999 | Kilmarnock FC | - | Dundee FC | 0:2 | ||||
| 10. Jornada | 16.10.1999 | Kilmarnock FC | - | Rangers FC | 1:1 | ||||
| 28. Jornada | 25.03.2000 | Kilmarnock FC | - | Hibernian FC | 1:0 | ||||
| 34. Jornada | 07.05.2000 | Kilmarnock FC | - | Rangers FC | 0:2 | ||||
| 35. Jornada | 14.05.2000 | Aberdeen FC | - | Kilmarnock FC | 5:1 |
Escocia