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 | ||||
8. Round | 19/10/1999 | Motherwell FC | - | Aberdeen FC | 5:6 | ||||
11. Round | 22/10/1999 | Aberdeen FC | - | Kilmarnock FC | 2:2 | ||||
12. Round | 29/10/1999 | Aberdeen FC | - | Rangers FC | 1:5 | ||||
13. Round | 05/11/1999 | Dundee United | - | Aberdeen FC | 3:1 |