2. Round | 10/08/2019 | St. Johnstone FC | - | Livingston FC | 2:2 | ||||
4. Round | 31/08/2019 | Livingston FC | - | St. Mirren FC | 2:1 | ||||
6. Round | 21/09/2019 | Livingston FC | - | Aberdeen FC | 0:2 | ||||
7. Round | 28/09/2019 | Hamilton Academical | - | Livingston FC | 2:1 | ||||
10. Round | 26/10/2019 | Livingston FC | - | Heart of Midlothian | 0:0 | ||||
11. Round | 30/10/2019 | Hibernian FC | - | Livingston FC | 2:2 | ||||
12. Round | 02/11/2019 | Motherwell FC | - | Livingston FC | 2:1 | ||||
14. Round | 23/11/2019 | Celtic FC | - | Livingston FC | 4:0 |