| 1. Round | 16/10/2020 | Heart of Midlothian | - | Dundee FC | 6:2 |  |
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| 2. Round | 23/10/2020 | Arbroath FC | - | Heart of Midlothian | 0:1 | ||||
| 7. Round | 12/12/2020 | Heart of Midlothian | - | Queen Of The South | 6:1 | |
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| 13. Round | 16/01/2021 | Alloa Athletic | - | Heart of Midlothian | 1:3 | |
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| 14. Round | 23/01/2021 | Heart of Midlothian | - | Raith Rovers | 2:3 | ||||
| 8. Round | 26/01/2021 | Raith Rovers | - | Heart of Midlothian | 0:4 |
England