| 3. Round | 19/08/2023 | Kelty Hearts | - | Alloa Athletic | 2:1 |  |
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| 4. Round | 26/08/2023 | Alloa Athletic | - | Falkirk FC | 1:4 | |
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| 5. Round | 02/09/2023 | Alloa Athletic | - | Cove Rangers | 1:0 | ||||
| 6. Round | 16/09/2023 | Hamilton Academical | - | Alloa Athletic | 2:1 | ||||
| 7. Round | 23/09/2023 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
| 8. Round | 30/09/2023 | Alloa Athletic | - | Edinburgh City | 1:1 | |
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| 9. Round | 07/10/2023 | Montrose FC | - | Alloa Athletic | 2:1 | ||||
| 10. Round | 21/10/2023 | Alloa Athletic | - | Kelty Hearts | 3:1 |
England