1. Round | 04/08/2018 | Hamilton Academical | - | Heart of Midlothian | 1:4 | ||||
2. Round | 11/08/2018 | Heart of Midlothian | - | Celtic FC | 1:0 | ||||
9. Round | 20/10/2018 | Heart of Midlothian | - | Aberdeen FC | 2:1 | ||||
18. Round | 14/12/2018 | Livingston FC | - | Heart of Midlothian | 5:0 |