| 3. Ronde | 15.08.1999 | St. Johnstone FC | - | Kilmarnock FC | 2:0 | ||||
| 4. Ronde | 21.08.1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
| 5. Ronde | 29.08.1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
| 6. Ronde | 12.09.1999 | Kilmarnock FC | - | Celtic FC | 0:1 |  |
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| 7. Ronde | 19.09.1999 | Hibernian FC | - | Kilmarnock FC | 0:3 | ||||
| 16. Ronde | 27.11.1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 | ||||
| 19. Ronde | 18.12.1999 | Kilmarnock FC | - | St. Johnstone FC | 1:2 |  |
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| 20. Ronde | 27.12.1999 | Hibernian FC | - | Kilmarnock FC | 2:2 | ||||
| 29. Ronde | 02.04.2000 | Celtic FC | - | Kilmarnock FC | 4:2 | |
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| 30. Ronde | 08.04.2000 | Kilmarnock FC | - | Dundee United | 1:0 | ||||
| 26. Ronde | 12.04.2000 | Kilmarnock FC | - | Aberdeen FC | 1:0 | |
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| 31. Ronde | 16.04.2000 | Motherwell FC | - | Kilmarnock FC | 2:0 | ||||
| 32. Ronde | 22.04.2000 | Dundee FC | - | Kilmarnock FC | 1:2 | |
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| 33. Ronde | 29.04.2000 | Kilmarnock FC | - | Heart of Midlothian | 0:1 | ||||
| 34. Ronde | 07.05.2000 | Kilmarnock FC | - | Rangers FC | 0:2 | ||||
| 35. Ronde | 14.05.2000 | Aberdeen FC | - | Kilmarnock FC | 5:1 |
Schotland