| 2. Round | 23/10/2020 | Arbroath FC | - | Heart of Midlothian | 0:1 | ||||
| 4. Round | 07/11/2020 | Heart of Midlothian | - | Inverness CT | 2:1 | ||||
| 5. Round | 20/11/2020 | Dunfermline Athletic | - | Heart of Midlothian | 2:1 | ||||
| 7. Round | 12/12/2020 | Heart of Midlothian | - | Queen Of The South | 6:1 |  |
|||
| 9. Round | 26/12/2020 | Heart of Midlothian | - | Ayr United | 5:3 | ||||
| 10. Round | 29/12/2020 | Heart of Midlothian | - | Arbroath FC | 3:1 | ||||
| 13. Round | 16/01/2021 | Alloa Athletic | - | Heart of Midlothian | 1:3 | |
|||
| 14. Round | 23/01/2021 | Heart of Midlothian | - | Raith Rovers | 2:3 |
England