| 3. Ronde | 19.08.2023 | Kelty Hearts | - | Alloa Athletic | 2:1 |  |
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| 4. Ronde | 26.08.2023 | Alloa Athletic | - | Falkirk FC | 1:4 | |
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| 5. Ronde | 02.09.2023 | Alloa Athletic | - | Cove Rangers | 1:0 | ||||
| 6. Ronde | 16.09.2023 | Hamilton Academical | - | Alloa Athletic | 2:1 | ||||
| 7. Ronde | 23.09.2023 | Annan Athletic | - | Alloa Athletic | 1:1 | ||||
| 8. Ronde | 30.09.2023 | Alloa Athletic | - | Edinburgh City | 1:1 | |
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| 9. Ronde | 07.10.2023 | Montrose FC | - | Alloa Athletic | 2:1 | ||||
| 10. Ronde | 21.10.2023 | Alloa Athletic | - | Kelty Hearts | 3:1 |
Engeland