1. Round | 30/07/1999 | Dundee United | - | Dundee FC | 2:1 | ||||
2. Round | 07/08/1999 | Dundee FC | - | Hibernian FC | 3:4 | ||||
3. Round | 13/08/1999 | Aberdeen FC | - | Dundee FC | 0:2 | ||||
4. Round | 20/08/1999 | Dundee FC | - | Celtic FC | 1:2 | ||||
5. Round | 27/08/1999 | Motherwell FC | - | Dundee FC | 0:2 | ||||
6. Round | 10/09/1999 | Heart of Midlothian | - | Dundee FC | 4:0 | ||||
7. Round | 18/09/1999 | Dundee FC | - | St. Johnstone FC | 1:2 | ||||
11. Round | 22/10/1999 | Hibernian FC | - | Dundee FC | 5:2 | ||||
19. Round | 22/02/2000 | Dundee FC | - | Aberdeen FC | 1:3 | ||||
24. Round | 26/02/2000 | Dundee FC | - | Rangers FC | 1:7 | ||||
31. Round | 14/04/2000 | Celtic FC | - | Dundee FC | 2:2 | ||||
34. Round | 05/05/2000 | Dundee FC | - | Dundee United | 3:0 |