1. Round | 30/07/1999 | Dundee United | - | Dundee FC | 2:1 | ||||
2. Round | 06/08/1999 | Motherwell FC | - | Dundee United | 2:2 | ||||
3. Round | 14/08/1999 | Dundee United | - | Celtic FC | 2:1 | ||||
4. Round | 20/08/1999 | Rangers FC | - | Dundee United | 4:1 | ||||
5. Round | 28/08/1999 | Dundee United | - | Kilmarnock FC | 0:0 | ||||
6. Round | 10/09/1999 | Dundee United | - | Hibernian FC | 3:1 | ||||
8. Round | 24/09/1999 | Dundee United | - | Heart of Midlothian | 0:2 | ||||
13. Round | 05/11/1999 | Dundee United | - | Aberdeen FC | 3:1 |