| 1. Jornada | 31.07.1999 | Dundee United | - | Dundee FC | 2:1 | ||||
| 2. Jornada | 08.08.1999 | Dundee FC | - | Hibernian FC | 3:4 | ||||
| 3. Jornada | 14.08.1999 | Aberdeen FC | - | Dundee FC | 0:2 | ||||
| 4. Jornada | 21.08.1999 | Dundee FC | - | Celtic FC | 1:2 |  |
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| 5. Jornada | 28.08.1999 | Motherwell FC | - | Dundee FC | 0:2 | ||||
| 6. Jornada | 11.09.1999 | Heart of Midlothian | - | Dundee FC | 4:0 | |
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| 7. Jornada | 19.09.1999 | Dundee FC | - | St. Johnstone FC | 1:2 | ||||
| 11. Jornada | 23.10.1999 | Hibernian FC | - | Dundee FC | 5:2 | ||||
| 19. Jornada | 23.02.2000 | Dundee FC | - | Aberdeen FC | 1:3 | ||||
| 24. Jornada | 27.02.2000 | Dundee FC | - | Rangers FC | 1:7 | ||||
| 31. Jornada | 15.04.2000 | Celtic FC | - | Dundee FC | 2:2 | ||||
| 34. Jornada | 06.05.2000 | Dundee FC | - | Dundee United | 3:0 |
Escocia