1. Round | 31/07/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
2. Round | 15/08/1998 | Dundee United | - | Heart of Midlothian | 0:0 | ||||
3. Round | 21/08/1998 | Celtic FC | - | Dundee United | 2:1 | ||||
4. Round | 29/08/1998 | Motherwell FC | - | Dundee United | 1:0 | ||||
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 | ||||
19. Round | 19/12/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
26. Round | 29/12/1998 | Dundee United | - | Rangers FC | 1:2 | ||||
21. Round | 01/01/1999 | Dundee FC | - | Dundee United | 1:3 | ||||
22. Round | 29/01/1999 | Dundee United | - | Dunfermline Athletic | 1:1 |