| 1. Ronde | 31.07.1999 | Rangers FC | - | Kilmarnock FC | 2:1 | ||||
| 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 |  |
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| 5. Ronde | 28.08.1999 | Hibernian FC | - | Rangers FC | 0:1 | ||||
| 8. Ronde | 25.09.1999 | Rangers FC | - | St. Johnstone FC | 3:1 | ||||
| 9. Ronde | 02.10.1999 | Dundee FC | - | Rangers FC | 2:3 | ||||
| 12. Ronde | 30.10.1999 | Aberdeen FC | - | Rangers FC | 1:5 | ||||
| 14. Ronde | 20.11.1999 | Rangers FC | - | Hibernian FC | 2:0 | ||||
| 16. Ronde | 28.11.1999 | Rangers FC | - | Dundee FC | 1:2 |
Polen