| 1. Ronde | 31.07.1999 | Dundee United | - | Dundee FC | 2:1 | ||||
| 4. Ronde | 21.08.1999 | Dundee FC | - | Celtic FC | 1:2 |  |
|||
| 9. Ronde | 02.10.1999 | Dundee FC | - | Rangers FC | 2:3 | ||||
| 10. Ronde | 17.10.1999 | Dundee FC | - | Dundee United | 0:2 | ||||
| 11. Ronde | 23.10.1999 | Hibernian FC | - | Dundee FC | 5:2 | ||||
| 12. Ronde | 30.10.1999 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 20. Ronde | 27.12.1999 | Dundee FC | - | St. Johnstone FC | 1:1 | ||||
| 21. Ronde | 22.01.2000 | Heart of Midlothian | - | Dundee FC | 2:0 | ||||
| 23. Ronde | 12.02.2000 | Dundee FC | - | Celtic FC | 0:3 | ||||
| 24. Ronde | 27.02.2000 | Dundee FC | - | Rangers FC | 1:7 | ||||
| 15. Ronde | 01.03.2000 | Celtic FC | - | Dundee FC | 6:2 | ||||
| 25. Ronde | 04.03.2000 | Kilmarnock FC | - | Dundee FC | 2:2 | ||||
| 35. Ronde | 21.03.2000 | Hibernian FC | - | Dundee FC | 1:2 | ||||
| 36. Ronde | 21.05.2000 | Dundee FC | - | Aberdeen FC | 0:2 |
Schotland