| 3. Round | 24/08/1996 | Aberdeen FC | - | Heart of Midlothian | 4:0 |  |
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| 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 | ||||
| 12. Round | 15/11/1996 | Heart of Midlothian | - | Hibernian FC | 0:0 | ||||
| 14. Round | 29/11/1996 | Celtic FC | - | Heart of Midlothian | 2:2 | ||||
| 15. Round | 06/12/1996 | Heart of Midlothian | - | Raith Rovers | 0:0 | ||||
| 17. Round | 13/12/1996 | Kilmarnock FC | - | Heart of Midlothian | 2:0 | ||||
| 20. Round | 27/12/1996 | Heart of Midlothian | - | Motherwell FC | 4:1 |
Cyprus