| 4. Round | 06/11/2020 | Alloa Athletic | - | Dundee FC | 3:3 | ||||
| 5. Round | 21/11/2020 | Queen Of The South | - | Alloa Athletic | 2:0 | ||||
| 7. Round | 12/12/2020 | Arbroath FC | - | Alloa Athletic | 0:1 | ||||
| 13. Round | 16/01/2021 | Alloa Athletic | - | Heart of Midlothian | 1:3 | ||||
| 17. Round | 20/02/2021 | Dunfermline Athletic | - | Alloa Athletic | 2:1 | ||||
| 21. Round | 19/03/2021 | Alloa Athletic | - | Dundee FC | 0:3 | ||||
| 26. Round | 24/04/2021 | Greenock Morton FC | - | Alloa Athletic | 1:1 |
Scotland