1. Round | 31/07/1999 | Aberdeen FC | - | Celtic FC | 0:5 | ||||
2. Round | 06/08/1999 | Kilmarnock FC | - | Aberdeen FC | 2:0 | ||||
3. Round | 13/08/1999 | Aberdeen FC | - | Dundee FC | 0:2 | ||||
4. Round | 21/08/1999 | Heart of Midlothian | - | Aberdeen FC | 3:0 | ||||
7. Round | 17/09/1999 | Aberdeen FC | - | Dundee United | 1:2 | ||||
9. Round | 01/10/1999 | Aberdeen FC | - | Hibernian FC | 2:2 | ||||
10. Round | 15/10/1999 | Celtic FC | - | Aberdeen FC | 7:0 | ||||
26. Round | 11/04/2000 | Kilmarnock FC | - | Aberdeen FC | 1:0 | ||||
27. Round | 17/04/2000 | Aberdeen FC | - | Dundee FC | 0:1 | ||||
32. Round | 21/04/2000 | Aberdeen FC | - | Motherwell FC | 2:1 | ||||
33. Round | 28/04/2000 | Hibernian FC | - | Aberdeen FC | 1:0 | ||||
30. Round | 01/05/2000 | St. Johnstone FC | - | Aberdeen FC | 2:1 | ||||
34. Round | 05/05/2000 | Celtic FC | - | Aberdeen FC | 5:1 | ||||
35. Round | 13/05/2000 | Aberdeen FC | - | Kilmarnock FC | 5:1 |