2. Round | 06/08/1999 | Heart of Midlothian | - | Rangers FC | 0:4 | ||||
3. Round | 14/08/1999 | Rangers FC | - | Motherwell FC | 4:1 | ||||
4. Round | 20/08/1999 | Rangers FC | - | Dundee United | 4:1 | ||||
5. Round | 27/08/1999 | Hibernian FC | - | Rangers FC | 0:1 | ||||
6. Round | 10/09/1999 | Rangers FC | - | Aberdeen FC | 3:0 | ||||
8. Round | 24/09/1999 | Rangers FC | - | St. Johnstone FC | 3:1 | ||||
9. Round | 01/10/1999 | Dundee FC | - | Rangers FC | 2:3 | ||||
10. Round | 15/10/1999 | Kilmarnock FC | - | Rangers FC | 1:1 | ||||
12. Round | 29/10/1999 | Aberdeen FC | - | Rangers FC | 1:5 |