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 | ||||
8. Round | 25/09/1998 | St. Johnstone FC | - | Dundee United | 1:3 | ||||
9. Round | 03/10/1998 | Dundee United | - | Aberdeen FC | 1:0 | ||||
12. Round | 30/10/1998 | Rangers FC | - | Dundee United | 2:1 | ||||
13. Round | 06/11/1998 | Dundee United | - | Motherwell FC | 2:2 | ||||
14. Round | 14/11/1998 | Dunfermline Athletic | - | Dundee United | 2:1 | ||||
15. Round | 21/11/1998 | Dundee United | - | Dundee FC | 0:1 | ||||
16. Round | 27/11/1998 | Aberdeen FC | - | Dundee United | 0:3 | ||||
17. Round | 04/12/1998 | Dundee United | - | St. Johnstone FC | 1:1 | ||||
18. Round | 11/12/1998 | Dundee United | - | Celtic FC | 1:1 | ||||
19. Round | 19/12/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
20. Round | 25/12/1998 | Motherwell 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 |