2. Ronde | 07.08.1999 | Heart of Midlothian | - | Rangers FC | 0:4 | ||||
3. Ronde | 15.08.1999 | Rangers FC | - | Motherwell FC | 4:1 | ||||
4. Ronde | 21.08.1999 | Rangers FC | - | Dundee United | 4:1 | ||||
5. Ronde | 28.08.1999 | Hibernian FC | - | Rangers FC | 0:1 | ||||
6. Ronde | 11.09.1999 | Rangers FC | - | Aberdeen FC | 3:0 | ||||
8. Ronde | 25.09.1999 | Rangers FC | - | St. Johnstone FC | 3:1 | ||||
9. Ronde | 02.10.1999 | Dundee FC | - | Rangers FC | 2:3 | ||||
10. Ronde | 16.10.1999 | Kilmarnock FC | - | Rangers FC | 1:1 | ||||
12. Ronde | 30.10.1999 | Aberdeen FC | - | Rangers FC | 1:5 |