| 2. Round | 16/08/1996 | Heart of Midlothian | - | Kilmarnock FC | 3:2 | ||||
| 3. Round | 24/08/1996 | Aberdeen FC | - | Heart of Midlothian | 4:0 | ||||
| 5. Round | 13/09/1996 | Rangers FC | - | Heart of Midlothian | 3:0 | ||||
| 15. Round | 06/12/1996 | Heart of Midlothian | - | Raith Rovers | 0:0 | ||||
| 16. Round | 10/12/1996 | Heart of Midlothian | - | Aberdeen FC | 1:2 | ||||
| 17. Round | 13/12/1996 | Kilmarnock FC | - | Heart of Midlothian | 2:0 | ||||
| 34. Round | 18/04/1997 | Heart of Midlothian | - | Dunfermline Athletic | 1:1 | ||||
| 35. Round | 02/05/1997 | Dundee United | - | Heart of Midlothian | 1:0 |  |
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| 36. Round | 09/05/1997 | Heart of Midlothian | - | Rangers FC | 3:1 |
Scotland