3. Round | 24/08/2019 | Ross County FC | - | Livingston FC | 1:4 | ||||
4. Round | 31/08/2019 | Livingston FC | - | St. Mirren FC | 2:1 | ||||
5. Round | 14/09/2019 | Rangers FC | - | Livingston FC | 3:1 | ||||
6. Round | 21/09/2019 | Livingston FC | - | Aberdeen FC | 0:2 | ||||
15. Round | 30/11/2019 | Livingston FC | - | Hamilton Academical | 0:0 | ||||
16. Round | 04/12/2019 | Heart of Midlothian | - | Livingston FC | 1:1 | ||||
19. Round | 21/12/2019 | Livingston FC | - | Ross County FC | 4:0 | ||||
20. Round | 26/12/2019 | Aberdeen FC | - | Livingston FC | 2:1 | ||||
21. Round | 29/12/2019 | Livingston FC | - | Hibernian FC | 2:0 | ||||
22. Round | 22/01/2020 | Livingston FC | - | St. Johnstone FC | 1:0 |