1. Round | 01/08/1998 | Heart of Midlothian | - | Rangers FC | 2:1 | ||||
3. Round | 21/08/1998 | Kilmarnock FC | - | Rangers FC | 1:3 | ||||
4. Round | 28/08/1998 | Rangers FC | - | St. Johnstone FC | 4:0 | ||||
5. Round | 11/09/1998 | Dundee United | - | Rangers FC | 0:0 | ||||
6. Round | 19/09/1998 | Rangers FC | - | Celtic FC | 0:0 | ||||
7. Round | 22/09/1998 | Aberdeen FC | - | Rangers FC | 1:1 | ||||
8. Round | 25/09/1998 | Dunfermline Athletic | - | Rangers FC | 0:2 | ||||
29. Round | 03/04/1999 | St. Johnstone FC | - | Rangers FC | 3:1 |