| 1. Round | 30/07/2022 | Dunfermline Athletic | - | Alloa Athletic | 1:0 | ||||
| 2. Round | 06/08/2022 | Alloa Athletic | - | Kelty Hearts | 3:1 |  |
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| 3. Round | 13/08/2022 | Alloa Athletic | - | FC Edinburgh | 2:4 | ||||
| 4. Round | 20/08/2022 | Airdrieonians FC | - | Alloa Athletic | 2:0 | ||||
| 5. Round | 27/08/2022 | Alloa Athletic | - | Peterhead FC | 5:0 | |
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| 6. Round | 03/09/2022 | Clyde FC | - | Alloa Athletic | 2:4 | |
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| 8. Round | 17/09/2022 | Alloa Athletic | - | Montrose FC | 2:1 | |
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| 9. Round | 01/10/2022 | Queen Of The South | - | Alloa Athletic | 1:1 | ||||
| 10. Round | 08/10/2022 | Alloa Athletic | - | Dunfermline Athletic | 0:3 | ||||
| 11. Round | 15/10/2022 | Alloa Athletic | - | Airdrieonians FC | 2:0 | ||||
| 12. Round | 22/10/2022 | Peterhead FC | - | Alloa Athletic | 0:2 | ||||
| 13. Round | 29/10/2022 | Alloa Athletic | - | Clyde FC | 2:1 | ||||
| 15. Round | 12/11/2022 | Alloa Athletic | - | Queen Of The South | 5:1 | ||||
| 19. Round | 23/12/2022 | Clyde FC | - | Alloa Athletic | 2:2 | ||||
| 21. Round | 07/01/2023 | Queen Of The South | - | Alloa Athletic | 1:2 |
Scotland