| 1. Round | 17/10/2020 | Greenock Morton FC | - | Alloa Athletic | 1:0 | ||||
| 2. Round | 24/10/2020 | Alloa Athletic | - | Dunfermline Athletic | 1:4 | ||||
| 4. Round | 06/11/2020 | Alloa Athletic | - | Dundee FC | 3:3 |  |
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| 5. Round | 21/11/2020 | Queen Of The South | - | Alloa Athletic | 2:0 | ||||
| 3. Round | 24/11/2020 | Heart of Midlothian | - | Alloa Athletic | 3:0 | ||||
| 6. Round | 05/12/2020 | Alloa Athletic | - | Ayr United | 0:2 | ||||
| 7. Round | 12/12/2020 | Arbroath FC | - | Alloa Athletic | 0:1 | ||||
| 8. Round | 19/12/2020 | Alloa Athletic | - | Inverness CT | 2:1 | |
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| 9. Round | 26/12/2020 | Alloa Athletic | - | Raith Rovers | 2:5 | ||||
| 10. Round | 29/12/2020 | Dundee FC | - | Alloa Athletic | 3:1 | ||||
| 11. Round | 02/01/2021 | Alloa Athletic | - | Greenock Morton FC | 1:1 | |
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| 13. Round | 16/01/2021 | Alloa Athletic | - | Heart of Midlothian | 1:3 | ||||
| 16. Round | 13/02/2021 | Alloa Athletic | - | Arbroath FC | 1:1 | ||||
| 17. Round | 20/02/2021 | Dunfermline Athletic | - | Alloa Athletic | 2:1 | ||||
| 23. Round | 03/04/2021 | Arbroath FC | - | Alloa Athletic | 2:1 | ||||
| 25. Round | 17/04/2021 | Alloa Athletic | - | Raith Rovers | 1:2 |
Scotland