1. Round | 31/07/1998 | Kilmarnock FC | - | Dundee United | 2:0 | ||||
3. Round | 21/08/1998 | Celtic FC | - | Dundee United | 2:1 | ||||
4. Round | 29/08/1998 | Motherwell FC | - | Dundee United | 1:0 | ||||
10. Round | 16/10/1998 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
35. Round | 14/05/1999 | Heart of Midlothian | - | Dundee United | 4:1 |