| 1. Ronde | 16.10.2020 | Heart of Midlothian | - | Dundee FC | 6:2 | ||||
| 2. Ronde | 23.10.2020 | Arbroath FC | - | Heart of Midlothian | 0:1 |  |
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| 4. Ronde | 07.11.2020 | Heart of Midlothian | - | Inverness CT | 2:1 | ||||
| 5. Ronde | 20.11.2020 | Dunfermline Athletic | - | Heart of Midlothian | 2:1 | ||||
| 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 | |
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| 10. Ronde | 29.12.2020 | Heart of Midlothian | - | Arbroath FC | 3:1 |  |
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| 11. Ronde | 02.01.2021 | Dundee FC | - | Heart of Midlothian | 3:1 |
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