| 1. Round | 16/10/2020 | Heart of Midlothian | - | Dundee FC | 6:2 | ||||
| 2. Round | 23/10/2020 | Arbroath FC | - | Heart of Midlothian | 0:1 |  |
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| 4. Round | 07/11/2020 | Heart of Midlothian | - | Inverness CT | 2:1 | ||||
| 5. Round | 20/11/2020 | Dunfermline Athletic | - | Heart of Midlothian | 2:1 | ||||
| 6. Round | 05/12/2020 | Greenock Morton FC | - | Heart of Midlothian | 0:2 | ||||
| 9. Round | 26/12/2020 | Heart of Midlothian | - | Ayr United | 5:3 | |
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| 10. Round | 29/12/2020 | Heart of Midlothian | - | Arbroath FC | 3:1 |  |
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| 11. Round | 02/01/2021 | Dundee FC | - | Heart of Midlothian | 3:1 |
Scotland