| Grupo D | 15.07.2023 | Stranraer FC | - | Ross County FC | 1:5 | ||||
| Grupo D | 22.07.2023 | Ross County FC | - | Greenock Morton FC | 2:1 | ||||
| Grupo D | 26.07.2023 | Edinburgh City | - | Ross County FC | 1:3 | ||||
| Grupo D | 29.07.2023 | Ross County FC | - | Kelty Hearts | 3:4 pn. | ||||
| Octavos de final | 19.08.2023 | Airdrieonians FC | - | Ross County FC | 3:4 pró. |  |
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| Cuartos de final | 27.09.2023 | Ross County FC | - | Aberdeen FC | 1:2 | |
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