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 | ||||
11. Ronde | 22.12.1999 | Rangers FC | - | Heart of Midlothian | 1:0 | ||||
20. Ronde | 27.12.1999 | Celtic FC | - | Rangers FC | 1:1 |