| 11. Round | 02/01/2021 | Dundee FC | - | Heart of Midlothian | 3:1 | ||||
| 13. Round | 16/01/2021 | Alloa Athletic | - | Heart of Midlothian | 1:3 | ||||
| 8. Round | 26/01/2021 | Raith Rovers | - | Heart of Midlothian | 0:4 |  |
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| 12. Round | 30/01/2021 | Heart of Midlothian | - | Dunfermline Athletic | 1:0 | ||||
| 16. Round | 12/02/2021 | Queen Of The South | - | Heart of Midlothian | 1:1 | ||||
| 22. Round | 27/03/2021 | Heart of Midlothian | - | Queen Of The South | 2:3 | ||||
| 23. Round | 03/04/2021 | Dunfermline Athletic | - | Heart of Midlothian | 0:0 | ||||
| 24. Round | 09/04/2021 | Heart of Midlothian | - | Alloa Athletic | 6:0 | |
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| 27. Round | 30/04/2021 | Raith Rovers | - | Heart of Midlothian | 0:4 | |
Scotland