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 | ||||
10. Round | 15/10/1999 | Kilmarnock FC | - | Rangers FC | 1:1 | ||||
28. Round | 24/03/2000 | Kilmarnock FC | - | Hibernian FC | 1:0 | ||||
34. Round | 06/05/2000 | Kilmarnock FC | - | Rangers FC | 0:2 | ||||
35. Round | 13/05/2000 | Aberdeen FC | - | Kilmarnock FC | 5:1 |