| 2. Round | 16/08/1996 | Heart of Midlothian | - | Kilmarnock FC | 3:2 |  |
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| 4. Round | 06/09/1996 | Heart of Midlothian | - | Dundee United | 1:0 | ||||
| 1. Round | 09/09/1996 | Dunfermline Athletic | - | Heart of Midlothian | 2:1 | ||||
| 7. Round | 27/09/1996 | Hibernian FC | - | Heart of Midlothian | 1:3 | ||||
| 9. Round | 19/10/1996 | Heart of Midlothian | - | Celtic FC | 2:2 | ||||
| 10. Round | 25/10/1996 | Dundee United | - | Heart of Midlothian | 1:0 | ||||
| 11. Round | 01/11/1996 | Heart of Midlothian | - | Dunfermline Athletic | 2:0 | ||||
| 17. Round | 13/12/1996 | Kilmarnock FC | - | Heart of Midlothian | 2:0 |  |
England