1. Round | 31/07/1998 | Dundee FC | - | Aberdeen FC | 0:2 | ||||
2. Round | 14/08/1998 | Dunfermline Athletic | - | Dundee FC | 2:0 | ||||
3. Round | 22/08/1998 | Dundee FC | - | St. Johnstone FC | 0:1 | ||||
8. Round | 25/09/1998 | Dundee FC | - | Motherwell FC | 1:0 | ||||
9. Round | 03/10/1998 | Rangers FC | - | Dundee FC | 1:0 | ||||
12. Round | 30/10/1998 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
14. Round | 13/11/1998 | Dundee FC | - | Kilmarnock FC | 1:1 | ||||
15. Round | 21/11/1998 | Dundee United | - | Dundee FC | 0:1 | ||||
17. Round | 15/12/1998 | Motherwell FC | - | Dundee FC | 2:1 | ||||
21. Round | 01/01/1999 | Dundee FC | - | Dundee United | 1:3 | ||||
23. Round | 05/02/1999 | Dundee FC | - | Motherwell FC | 1:0 | ||||
24. Round | 19/02/1999 | Rangers FC | - | Dundee FC | 6:1 | ||||
25. Round | 26/02/1999 | Dundee FC | - | St. Johnstone FC | 0:1 | ||||
31. Round | 17/04/1999 | Dundee FC | - | Rangers FC | 1:1 | ||||
34. Round | 07/05/1999 | Aberdeen FC | - | Dundee FC | 1:2 | ||||
35. Round | 14/05/1999 | Dundee FC | - | Dunfermline Athletic | 3:1 |