4. Round | 20/08/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
32. Round | 21/04/2000 | Dundee FC | - | Kilmarnock FC | 1:2 | ||||
34. Round | 06/05/2000 | Kilmarnock FC | - | Rangers FC | 0:2 | ||||
35. Round | 13/05/2000 | Aberdeen FC | - | Kilmarnock FC | 5:1 | ||||
36. Round | 20/05/2000 | Kilmarnock FC | - | St. Johnstone FC | 3:2 |