| Group D | 15/07/2023 | Stranraer FC | - | Ross County FC | 1:5 | ||||
| Group D | 22/07/2023 | Ross County FC | - | Greenock Morton FC | 2:1 | ||||
| Group D | 26/07/2023 | Edinburgh City | - | Ross County FC | 1:3 | ||||
| Group D | 29/07/2023 | Ross County FC | - | Kelty Hearts | 3:4 pso | ||||
| Round of 16 | 19/08/2023 | Airdrieonians FC | - | Ross County FC | 3:4 aet | ||||
| Quarter-finals | 27/09/2023 | Ross County FC | - | Aberdeen FC | 1:2 |  |
England