| 8. Ronde | 25.09.1999 | Dundee United | - | Heart of Midlothian | 0:2 | ||||
| 10. Ronde | 17.10.1999 | Dundee FC | - | Dundee United | 0:2 | ||||
| 11. Ronde | 23.10.1999 | Dundee United | - | Motherwell FC | 0:2 | ||||
| 9. Ronde | 27.10.1999 | St. Johnstone FC | - | Dundee United | 0:1 | ||||
| 12. Ronde | 31.10.1999 | Hibernian FC | - | Dundee United | 3:2 | ||||
| 13. Ronde | 06.11.1999 | Dundee United | - | Aberdeen FC | 3:1 | ||||
| 14. Ronde | 20.11.1999 | Kilmarnock FC | - | Dundee United | 1:1 | ||||
| 16. Ronde | 27.11.1999 | Dundee United | - | St. Johnstone FC | 1:0 | ||||
| 17. Ronde | 05.12.1999 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 22. Ronde | 15.03.2000 | Dundee United | - | Kilmarnock FC | 2:2 | ||||
| 31. Ronde | 15.04.2000 | Dundee United | - | Rangers FC | 0:2 | ||||
| 26. Ronde | 19.04.2000 | Motherwell FC | - | Dundee United | 1:3 | ||||
| 32. Ronde | 22.04.2000 | Heart of Midlothian | - | Dundee United | 1:2 | ||||
| 33. Ronde | 29.04.2000 | Dundee United | - | St. Johnstone FC | 0:1 | ||||
| 36. Ronde | 21.05.2000 | Celtic FC | - | Dundee United | 2:0 |
Schotland