| 1. Round | 05/08/2023 | Queen Of The South | - | Alloa Athletic | 3:4 | ||||
| 2. Round | 12/08/2023 | Edinburgh City | - | Queen Of The South | 1:2 | ||||
| 3. Round | 19/08/2023 | Queen Of The South | - | Annan Athletic | 3:1 | ||||
| 4. Round | 26/08/2023 | Cove Rangers | - | Queen Of The South | 1:2 |  |
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| 9. Round | 07/10/2023 | Queen Of The South | - | Stirling Albion FC | 0:1 | ||||
| 10. Round | 21/10/2023 | Annan Athletic | - | Queen Of The South | 0:1 | ||||
| 11. Round | 28/10/2023 | Queen Of The South | - | Cove Rangers | 0:1 | ||||
| 12. Round | 04/11/2023 | Queen Of The South | - | Falkirk FC | 1:1 | ||||
| 22. Round | 27/01/2024 | Cove Rangers | - | Queen Of The South | 0:2 | ||||
| 23. Round | 03/02/2024 | Queen Of The South | - | Hamilton Academical | 0:2 | ||||
| 24. Round | 10/02/2024 | Kelty Hearts | - | Queen Of The South | 0:0 | ||||
| 25. Round | 17/02/2024 | Edinburgh City | - | Queen Of The South | 1:1 | ||||
| 26. Round | 24/02/2024 | Queen Of The South | - | Montrose FC | 2:3 | ||||
| 36. Round | 04/05/2024 | Montrose FC | - | Queen Of The South | 3:2 |
Germany