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 | ||||
5. Round | 15/09/2018 | Hibernian FC | - | Kilmarnock FC | 3:2 | ||||
6. Round | 23/09/2018 | Kilmarnock FC | - | Celtic FC | 2:1 | ||||
7. Round | 29/09/2018 | Kilmarnock FC | - | Motherwell FC | 3:1 | ||||
8. Round | 06/10/2018 | Dundee FC | - | Kilmarnock FC | 1:2 | ||||
9. Round | 20/10/2018 | St. Mirren FC | - | Kilmarnock FC | 1:2 | ||||
10. Round | 27/10/2018 | Kilmarnock FC | - | Hamilton Academical | 1:1 | ||||
11. Round | 31/10/2018 | Rangers FC | - | Kilmarnock FC | 1:1 | ||||
12. Round | 04/11/2018 | Kilmarnock FC | - | Aberdeen FC | 1:2 |