| 3. Jornada | 15.08.1999 | St. Johnstone FC | - | Kilmarnock FC | 2:0 | ||||
| 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 | ||||
| 16. Jornada | 27.11.1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 | ||||
| 19. Jornada | 18.12.1999 | Kilmarnock FC | - | St. Johnstone FC | 1:2 |  |
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| 20. Jornada | 27.12.1999 | Hibernian FC | - | Kilmarnock FC | 2:2 | ||||
| 29. Jornada | 02.04.2000 | Celtic FC | - | Kilmarnock FC | 4:2 | |
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| 30. Jornada | 08.04.2000 | Kilmarnock FC | - | Dundee United | 1:0 | ||||
| 26. Jornada | 12.04.2000 | Kilmarnock FC | - | Aberdeen FC | 1:0 | |
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| 31. Jornada | 16.04.2000 | Motherwell FC | - | Kilmarnock FC | 2:0 | ||||
| 32. Jornada | 22.04.2000 | Dundee FC | - | Kilmarnock FC | 1:2 | |
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| 33. Jornada | 29.04.2000 | Kilmarnock FC | - | Heart of Midlothian | 0:1 | ||||
| 34. Jornada | 07.05.2000 | Kilmarnock FC | - | Rangers FC | 0:2 | ||||
| 35. Jornada | 14.05.2000 | Aberdeen FC | - | Kilmarnock FC | 5:1 |
Escocia