| Grupo F | 15.07.2023 | Kilmarnock FC | - | Annan Athletic | 3:0 | ||||
| Grupo F | 22.07.2023 | Dunfermline Athletic | - | Kilmarnock FC | 0:2 | ||||
| Grupo F | 26.07.2023 | Kilmarnock FC | - | Raith Rovers | 4:5 pn. |  |
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| Grupo F | 29.07.2023 | Albion Rovers | - | Kilmarnock FC | 1:2 | |
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| Octavos de final | 20.08.2023 | Kilmarnock FC | - | Celtic FC | 1:0 |  |
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| Cuartos de final | 26.09.2023 | Kilmarnock FC | - | Heart of Midlothian | 1:2 |
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