1. Round | 04/08/2018 | Kilmarnock FC | - | St. Johnstone FC | 2:0 | ||||
2. Round | 11/08/2018 | Livingston FC | - | Kilmarnock FC | 0:0 | ||||
3. Round | 25/08/2018 | Kilmarnock FC | - | Heart of Midlothian | 0:1 | ||||
4. Round | 01/09/2018 | Aberdeen FC | - | Kilmarnock FC | 0:2 | ||||
13. Round | 10/11/2018 | Heart of Midlothian | - | Kilmarnock FC | 0:1 | ||||
16. Round | 05/12/2018 | Kilmarnock FC | - | Livingston FC | 2:0 |