7. Round | 18/09/1999 | Dundee FC | - | St. Johnstone FC | 1:2 | ||||
8. Round | 24/09/1999 | Kilmarnock FC | - | Dundee FC | 0:2 | ||||
9. Round | 01/10/1999 | Dundee FC | - | Rangers FC | 2:3 | ||||
10. Round | 16/10/1999 | Dundee FC | - | Dundee United | 0:2 | ||||
11. Round | 22/10/1999 | Hibernian FC | - | Dundee FC | 5:2 |