1. Round | 30/07/1999 | Hibernian FC | - | Motherwell FC | 2:2 | ||||
2. Round | 07/08/1999 | Dundee FC | - | Hibernian FC | 3:4 | ||||
3. Round | 13/08/1999 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
4. Round | 20/08/1999 | St. Johnstone FC | - | Hibernian FC | 1:1 | ||||
5. Round | 27/08/1999 | Hibernian FC | - | Rangers FC | 0:1 | ||||
6. Round | 10/09/1999 | Dundee United | - | Hibernian FC | 3:1 | ||||
7. Round | 18/09/1999 | Hibernian FC | - | Kilmarnock FC | 0:3 | ||||
12. Round | 30/10/1999 | Hibernian FC | - | Dundee United | 3:2 | ||||
14. Round | 19/11/1999 | Rangers FC | - | Hibernian FC | 2:0 | ||||
17. Round | 03/12/1999 | Celtic FC | - | Hibernian FC | 4:0 |