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 | ||||
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 | ||||
23. Round | 11/02/2000 | Kilmarnock FC | - | Motherwell FC | 0:2 | ||||
32. Round | 21/04/2000 | Dundee FC | - | Kilmarnock FC | 1:2 | ||||
34. Round | 06/05/2000 | Kilmarnock FC | - | Rangers FC | 0:2 |