8. Round | 05/10/2019 | Heart of Midlothian | - | Kilmarnock FC | 0:1 | ||||
10. Round | 26/10/2019 | Livingston FC | - | Heart of Midlothian | 0:0 | ||||
17. Round | 07/12/2019 | Motherwell FC | - | Heart of Midlothian | 1:0 | ||||
18. Round | 14/12/2019 | Heart of Midlothian | - | St. Johnstone FC | 0:1 | ||||
20. Round | 26/12/2019 | Heart of Midlothian | - | Hibernian FC | 0:2 |