| 1. Ronde | 16.10.2020 | Heart of Midlothian | - | Dundee FC | 6:2 | ||||
| 2. Ronde | 23.10.2020 | Arbroath FC | - | Heart of Midlothian | 0:1 | ||||
| 4. Ronde | 07.11.2020 | Heart of Midlothian | - | Inverness CT | 2:1 |  |
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| 3. Ronde | 24.11.2020 | Heart of Midlothian | - | Alloa Athletic | 3:0 |  |
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| 6. Ronde | 05.12.2020 | Greenock Morton FC | - | Heart of Midlothian | 0:2 | ||||
| 9. Ronde | 26.12.2020 | Heart of Midlothian | - | Ayr United | 5:3 | ||||
| 10. Ronde | 29.12.2020 | Heart of Midlothian | - | Arbroath FC | 3:1 | ||||
| 11. Ronde | 02.01.2021 | Dundee FC | - | Heart of Midlothian | 3:1 | ||||
| 19. Ronde | 06.03.2021 | Heart of Midlothian | - | Dundee FC | 2:1 |  |
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| 23. Ronde | 03.04.2021 | Dunfermline Athletic | - | Heart of Midlothian | 0:0 | ||||
| 24. Ronde | 09.04.2021 | Heart of Midlothian | - | Alloa Athletic | 6:0 | |
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| 26. Ronde | 24.04.2021 | Heart of Midlothian | - | Inverness CT | 3:0 | ||||
| 27. Ronde | 30.04.2021 | Raith Rovers | - | Heart of Midlothian | 0:4 |
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