| 2. Jornada | 07.08.1999 | Kilmarnock FC | - | Aberdeen FC | 2:0 | ||||
| 3. Jornada | 15.08.1999 | St. Johnstone FC | - | Kilmarnock FC | 2:0 | ||||
| 4. Jornada | 21.08.1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
| 16. Jornada | 27.11.1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 | ||||
| 18. Jornada | 11.12.1999 | Rangers FC | - | Kilmarnock FC | 1:0 |  |
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| 19. Jornada | 18.12.1999 | Kilmarnock FC | - | St. Johnstone FC | 1:2 | ||||
| 20. Jornada | 27.12.1999 | Hibernian FC | - | Kilmarnock FC | 2:2 | ||||
| 21. Jornada | 23.01.2000 | Kilmarnock FC | - | Celtic FC | 1:1 | ||||
| 22. Jornada | 15.03.2000 | Dundee United | - | Kilmarnock FC | 2:2 | ||||
| 35. Jornada | 14.05.2000 | Aberdeen FC | - | Kilmarnock FC | 5:1 | ||||
| 36. Jornada | 21.05.2000 | Kilmarnock FC | - | St. Johnstone FC | 3:2 |
Escocia