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 | ||||
34. Round | 07/05/1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
35. Round | 14/05/1999 | Heart of Midlothian | - | Dundee United | 4:1 | ||||
36. Round | 22/05/1999 | Dundee United | - | Celtic FC | 1:2 |