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 | ||||
11. Round | 21/12/1999 | Rangers FC | - | Heart of Midlothian | 1:0 | ||||
20. Round | 26/12/1999 | Celtic FC | - | Rangers FC | 1:1 |