| 1. Round | 17/10/2020 | Ayr United | - | Queen Of The South | 2:1 | ||||
| 2. Round | 24/10/2020 | Queen Of The South | - | Raith Rovers | 2:5 | ||||
| 4. Round | 07/11/2020 | Arbroath FC | - | Queen Of The South | 1:1 | ||||
| 8. Round | 19/12/2020 | Greenock Morton FC | - | Queen Of The South | 2:0 | ||||
| 9. Round | 26/12/2020 | Queen Of The South | - | Dundee FC | 1:3 | ||||
| 10. Round | 29/12/2020 | Raith Rovers | - | Queen Of The South | 0:2 |  |
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| 11. Round | 02/01/2021 | Queen Of The South | - | Ayr United | 3:2 | ||||
| 15. Round | 06/02/2021 | Alloa Athletic | - | Queen Of The South | 2:1 | ||||
| 16. Round | 12/02/2021 | Queen Of The South | - | Heart of Midlothian | 1:1 | ||||
| 12. Round | 17/02/2021 | Inverness CT | - | Queen Of The South | 0:1 | ||||
| 20. Round | 13/03/2021 | Queen Of The South | - | Alloa Athletic | 2:3 | ||||
| 27. Round | 30/04/2021 | Queen Of The South | - | Dundee FC | 0:2 |
England