1. Round | 31/07/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
3. Round | 21/08/1998 | Kilmarnock FC | - | Rangers FC | 1:3 | ||||
4. Round | 29/08/1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
7. Round | 22/09/1998 | Kilmarnock FC | - | Dundee FC | 2:1 | ||||
8. Round | 26/09/1998 | Aberdeen FC | - | Kilmarnock FC | 0:1 | ||||
10. Round | 16/10/1998 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
11. Round | 23/10/1998 | Kilmarnock FC | - | St. Johnstone FC | 2:2 | ||||
15. Round | 20/11/1998 | Kilmarnock FC | - | Motherwell FC | 0:0 | ||||
22. Round | 29/01/1999 | Kilmarnock FC | - | Dundee FC | 0:0 | ||||
23. Round | 05/02/1999 | Aberdeen FC | - | Kilmarnock FC | 2:1 | ||||
26. Round | 16/02/1999 | Celtic FC | - | Kilmarnock FC | 1:0 | ||||
25. Round | 27/02/1999 | Kilmarnock FC | - | Rangers FC | 0:5 | ||||
28. Round | 20/03/1999 | Kilmarnock FC | - | Celtic FC | 0:0 | ||||
30. Round | 09/04/1999 | Kilmarnock FC | - | Aberdeen FC | 4:2 | ||||
33. Round | 30/04/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
34. Round | 07/05/1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
36. Round | 22/05/1999 | Rangers FC | - | Kilmarnock FC | 1:1 |