| 1. Round | 01/08/1998 | Heart of Midlothian | - | Rangers FC | 2:1 | ||||
| 13. Round | 07/11/1998 | St. Johnstone FC | - | Rangers FC | 0:7 | ||||
| 14. Round | 13/11/1998 | Rangers FC | - | Aberdeen FC | 2:1 | ||||
| 15. Round | 20/11/1998 | Celtic FC | - | Rangers FC | 5:1 | ||||
| 17. Round | 04/12/1998 | Rangers FC | - | Dunfermline Athletic | 1:1 | ||||
| 18. Round | 11/12/1998 | Rangers FC | - | Kilmarnock FC | 1:0 | ||||
| 19. Round | 18/12/1998 | Heart of Midlothian | - | Rangers FC | 2:3 |
Finland