| 1. Round | 30/07/1999 | Dundee United | - | Dundee FC | 2:1 | ||||
| 2. Round | 06/08/1999 | Motherwell FC | - | Dundee United | 2:2 | ||||
| 7. Round | 17/09/1999 | Aberdeen FC | - | Dundee United | 1:2 | ||||
| 9. Round | 26/10/1999 | St. Johnstone FC | - | Dundee United | 0:1 | ||||
| 12. Round | 30/10/1999 | Hibernian FC | - | Dundee United | 3:2 | ||||
| 13. Round | 05/11/1999 | Dundee United | - | Aberdeen FC | 3:1 | ||||
| 14. Round | 19/11/1999 | Kilmarnock FC | - | Dundee United | 1:1 | ||||
| 16. Round | 26/11/1999 | Dundee United | - | St. Johnstone FC | 1:0 | ||||
| 17. Round | 04/12/1999 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 18. Round | 11/12/1999 | Dundee United | - | Dundee FC | 1:0 | ||||
| 19. Round | 17/12/1999 | Celtic FC | - | Dundee United | 4:1 | ||||
| 20. Round | 26/12/1999 | Aberdeen FC | - | Dundee United | 3:1 | ||||
| 21. Round | 21/01/2000 | Dundee United | - | Hibernian FC | 0:0 |
Ireland