| 1. Jornada | 31.07.1999 | Rangers FC | - | Kilmarnock FC | 2:1 |  |
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| 2. Jornada | 07.08.1999 | Kilmarnock FC | - | Aberdeen FC | 2:0 |  |
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| 3. Jornada | 15.08.1999 | St. Johnstone FC | - | Kilmarnock FC | 2:0 | ||||
| 12. Jornada | 30.10.1999 | Celtic FC | - | Kilmarnock FC | 5:1 | ||||
| 13. Jornada | 06.11.1999 | Kilmarnock FC | - | Hibernian 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 | ||||
| 19. Jornada | 18.12.1999 | Kilmarnock FC | - | St. Johnstone FC | 1:2 | ||||
| 36. Jornada | 21.05.2000 | Kilmarnock FC | - | St. Johnstone FC | 3:2 |
Escocia