| 2. Round | 16/08/1996 | Heart of Midlothian | - | Kilmarnock FC | 3:2 | ||||
| 3. Round | 24/08/1996 | Aberdeen FC | - | Heart of Midlothian | 4:0 | ||||
| 1. Round | 09/09/1996 | Dunfermline Athletic | - | Heart of Midlothian | 2:1 |  |
|||
| 6. Round | 20/09/1996 | Heart of Midlothian | - | Motherwell FC | 1:1 | ||||
| 8. Round | 11/10/1996 | Raith Rovers | - | Heart of Midlothian | 1:1 | ||||
| 10. Round | 25/10/1996 | Dundee United | - | Heart of Midlothian | 1:0 | |
|||
| 11. Round | 01/11/1996 | Heart of Midlothian | - | Dunfermline Athletic | 2:0 | ||||
| 13. Round | 10/11/1996 | Motherwell FC | - | Heart of Midlothian | 0:2 | ||||
| 16. Round | 10/12/1996 | Heart of Midlothian | - | Aberdeen FC | 1:2 | ||||
| 17. Round | 13/12/1996 | Kilmarnock FC | - | Heart of Midlothian | 2:0 |
Scotland