2. Round | 15/08/1998 | Dundee United | - | Heart of Midlothian | 0:0 | ||||
5. Round | 11/09/1998 | Dundee United | - | Rangers FC | 0:0 | ||||
6. Round | 18/09/1998 | Dundee FC | - | Dundee United | 2:2 | ||||
7. Round | 22/09/1998 | Dundee United | - | Dunfermline Athletic | 1:1 | ||||
9. Round | 03/10/1998 | Dundee United | - | Aberdeen FC | 1:0 | ||||
10. Round | 16/10/1998 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
24. Round | 19/02/1999 | Dundee United | - | Aberdeen FC | 3:0 | ||||
25. Round | 26/02/1999 | Celtic FC | - | Dundee United | 2:1 |