| 1. Round | 30/07/1999 | Rangers FC | - | Kilmarnock FC | 2:1 | ||||
| 2. Round | 06/08/1999 | Kilmarnock FC | - | Aberdeen FC | 2:0 | ||||
| 3. Round | 14/08/1999 | St. Johnstone FC | - | Kilmarnock FC | 2:0 | ||||
| 4. Round | 20/08/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
| 5. Round | 28/08/1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
| 6. Round | 11/09/1999 | Kilmarnock FC | - | Celtic FC | 0:1 | ||||
| 7. Round | 18/09/1999 | Hibernian FC | - | Kilmarnock FC | 0:3 | ||||
| 8. Round | 24/09/1999 | Kilmarnock FC | - | Dundee FC | 0:2 | ||||
| 13. Round | 05/11/1999 | Kilmarnock FC | - | Hibernian FC | 0:2 | ||||
| 14. Round | 19/11/1999 | Kilmarnock FC | - | Dundee United | 1:1 | ||||
| 16. Round | 26/11/1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 | ||||
| 18. Round | 10/12/1999 | Rangers FC | - | Kilmarnock FC | 1:0 | ||||
| 19. Round | 17/12/1999 | Kilmarnock FC | - | St. Johnstone FC | 1:2 | ||||
| 20. Round | 26/12/1999 | Hibernian FC | - | Kilmarnock FC | 2:2 | ||||
| 21. Round | 22/01/2000 | Kilmarnock FC | - | Celtic FC | 1:1 | ||||
| 17. Round | 25/01/2000 | Dundee FC | - | Kilmarnock FC | 0:0 | ||||
| 23. Round | 11/02/2000 | Kilmarnock FC | - | Motherwell FC | 0:2 | ||||
| 36. Round | 20/05/2000 | Kilmarnock FC | - | St. Johnstone FC | 3:2 |
Scotland