1. Round | 04/08/2019 | Kilmarnock FC | - | Rangers FC | 1:2 | ||||
2. Round | 10/08/2019 | Hamilton Academical | - | Kilmarnock FC | 2:0 | ||||
22. Round | 22/01/2020 | Kilmarnock FC | - | Celtic FC | 1:3 | ||||
23. Round | 25/01/2020 | St. Johnstone FC | - | Kilmarnock FC | 2:1 | ||||
24. Round | 01/02/2020 | Kilmarnock FC | - | Ross County FC | 3:1 | ||||
25. Round | 05/02/2020 | Heart of Midlothian | - | Kilmarnock FC | 2:3 | ||||
27. Round | 16/02/2020 | Kilmarnock FC | - | Hibernian FC | 1:2 | ||||
28. Round | 23/02/2020 | Celtic FC | - | Kilmarnock FC | 3:1 | ||||
29. Round | 04/03/2020 | Kilmarnock FC | - | Aberdeen FC | 2:2 | ||||
30. Round | 07/03/2020 | Hamilton Academical | - | Kilmarnock FC | 1:0 |