| Group F | 15/07/2023 | Kilmarnock FC | - | Annan Athletic | 3:0 | ||||
| Group F | 22/07/2023 | Dunfermline Athletic | - | Kilmarnock FC | 0:2 | ||||
| Group F | 26/07/2023 | Kilmarnock FC | - | Raith Rovers | 4:5 pso | ||||
| Group F | 29/07/2023 | Albion Rovers | - | Kilmarnock FC | 1:2 | ||||
| Round of 16 | 20/08/2023 | Kilmarnock FC | - | Celtic FC | 1:0 | ||||
| Quarter-finals | 26/09/2023 | Kilmarnock FC | - | Heart of Midlothian | 1:2 |
Northern Ireland
Scotland 