| 12. Round | 30/10/1999 | Hibernian FC | - | Dundee United | 3:2 | ||||
| 13. Round | 05/11/1999 | Dundee United | - | Aberdeen FC | 3:1 | ||||
| 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 | ||||
| 24. Round | 25/02/2000 | St. Johnstone FC | - | Dundee United | 2:0 | ||||
| 29. Round | 31/03/2000 | Hibernian FC | - | Dundee United | 1:0 | ||||
| 31. Round | 14/04/2000 | Dundee United | - | Rangers FC | 0:2 | ||||
| 26. Round | 18/04/2000 | Motherwell FC | - | Dundee United | 1:3 | ||||
| 32. Round | 21/04/2000 | Heart of Midlothian | - | Dundee United | 1:2 | ||||
| 33. Round | 28/04/2000 | Dundee United | - | St. Johnstone FC | 0:1 | ||||
| 27. Round | 01/05/2000 | Dundee United | - | Celtic FC | 0:1 | ||||
| 34. Round | 05/05/2000 | Dundee FC | - | Dundee United | 3:0 | ||||
| 35. Round | 12/05/2000 | Dundee United | - | Motherwell FC | 1:2 | ||||
| 36. Round | 20/05/2000 | Celtic FC | - | Dundee United | 2:0 |
Scotland