| 1. Ronde | 31.07.1999 | Rangers FC | - | Kilmarnock FC | 2:1 | ||||
| 2. Ronde | 07.08.1999 | Kilmarnock FC | - | Aberdeen FC | 2:0 | ||||
| 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 | ||||
| 7. Ronde | 19.09.1999 | Hibernian FC | - | Kilmarnock FC | 0:3 | ||||
| 8. Ronde | 25.09.1999 | Kilmarnock FC | - | Dundee FC | 0:2 | ||||
| 13. Ronde | 06.11.1999 | Kilmarnock FC | - | Hibernian FC | 0:2 | ||||
| 14. Ronde | 20.11.1999 | Kilmarnock FC | - | Dundee United | 1:1 | ||||
| 16. Ronde | 27.11.1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 | ||||
| 18. Ronde | 11.12.1999 | Rangers FC | - | Kilmarnock FC | 1:0 | ||||
| 19. Ronde | 18.12.1999 | Kilmarnock FC | - | St. Johnstone FC | 1:2 | ||||
| 20. Ronde | 27.12.1999 | Hibernian FC | - | Kilmarnock FC | 2:2 | ||||
| 21. Ronde | 23.01.2000 | Kilmarnock FC | - | Celtic FC | 1:1 | ||||
| 17. Ronde | 26.01.2000 | Dundee FC | - | Kilmarnock FC | 0:0 | ||||
| 23. Ronde | 12.02.2000 | Kilmarnock FC | - | Motherwell FC | 0:2 | ||||
| 36. Ronde | 21.05.2000 | Kilmarnock FC | - | St. Johnstone FC | 3:2 |
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