1. Round | 31/07/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
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 | ||||
8. Round | 25/09/1998 | St. Johnstone FC | - | Dundee United | 1:3 |