| 1. Round | 20/04/2019 | Kilmarnock FC | - | Aberdeen FC | 0:1 |  |
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| 2. Round | 27/04/2019 | Celtic FC | - | Kilmarnock FC | 1:0 | ||||
| 3. Round | 04/05/2019 | Heart of Midlothian | - | Kilmarnock FC | 0:1 | ||||
| 4. Round | 11/05/2019 | Kilmarnock FC | - | Hibernian FC | 1:0 | ||||
| 5. Round | 19/05/2019 | Kilmarnock FC | - | Rangers FC | 2:1 |
Scotland