1. Round | 31/07/1999 | Aberdeen FC | - | Celtic FC | 0:5 | ||||
2. Round | 06/08/1999 | Kilmarnock FC | - | Aberdeen FC | 2:0 | ||||
6. Round | 10/09/1999 | Rangers FC | - | 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 | ||||
13. Round | 05/11/1999 | Dundee United | - | Aberdeen FC | 3:1 |