| 1. Jornada | 31.07.1999 | Dundee United | - | Dundee FC | 2:1 | ||||
| 2. Jornada | 07.08.1999 | Motherwell FC | - | Dundee United | 2:2 | ||||
| 7. Jornada | 18.09.1999 | Aberdeen FC | - | Dundee United | 1:2 | ||||
| 9. Jornada | 27.10.1999 | St. Johnstone FC | - | Dundee United | 0:1 | ||||
| 12. Jornada | 31.10.1999 | Hibernian FC | - | Dundee United | 3:2 | ||||
| 13. Jornada | 06.11.1999 | Dundee United | - | Aberdeen FC | 3:1 | ||||
| 14. Jornada | 20.11.1999 | Kilmarnock FC | - | Dundee United | 1:1 | ||||
| 16. Jornada | 27.11.1999 | Dundee United | - | St. Johnstone FC | 1:0 | ||||
| 17. Jornada | 05.12.1999 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 18. Jornada | 12.12.1999 | Dundee United | - | Dundee FC | 1:0 | ||||
| 19. Jornada | 18.12.1999 | Celtic FC | - | Dundee United | 4:1 | ||||
| 20. Jornada | 27.12.1999 | Aberdeen FC | - | Dundee United | 3:1 | ||||
| 21. Jornada | 22.01.2000 | Dundee United | - | Hibernian FC | 0:0 |
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