| 13. Round | 16/01/2021 | Alloa Athletic | - | Heart of Midlothian | 1:3 | ||||
| 14. Round | 23/01/2021 | Heart of Midlothian | - | Raith Rovers | 2:3 | ||||
| 8. Round | 26/01/2021 | Raith Rovers | - | Heart of Midlothian | 0:4 | ||||
| 12. Round | 30/01/2021 | Heart of Midlothian | - | Dunfermline Athletic | 1:0 | ||||
| 15. Round | 05/02/2021 | Ayr United | - | Heart of Midlothian | 0:1 | ||||
| 16. Round | 12/02/2021 | Queen Of The South | - | Heart of Midlothian | 1:1 | ||||
| 17. Round | 20/02/2021 | Heart of Midlothian | - | Greenock Morton FC | 1:1 | ||||
| 18. Round | 26/02/2021 | Inverness CT | - | Heart of Midlothian | 1:1 | ||||
| 19. Round | 06/03/2021 | Heart of Midlothian | - | Dundee FC | 2:1 | ||||
| 20. Round | 13/03/2021 | Heart of Midlothian | - | Ayr United | 2:0 | ||||
| 21. Round | 20/03/2021 | Arbroath FC | - | Heart of Midlothian | 0:0 | ||||
| 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 | ||||
| 26. Round | 24/04/2021 | Heart of Midlothian | - | Inverness CT | 3:0 |  |
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| 27. Round | 30/04/2021 | Raith Rovers | - | Heart of Midlothian | 0:4 | |
Scotland
