| 4. Round | 16/08/2020 | Livingston FC | - | Rangers FC | 0:0 | ||||
| 12. Round | 25/10/2020 | Rangers FC | - | Livingston FC | 2:0 | ||||
| 13. Round | 31/10/2020 | Livingston FC | - | Motherwell FC | 0:2 | ||||
| 14. Round | 06/11/2020 | Ross County FC | - | Livingston FC | 1:1 | ||||
| 15. Round | 21/11/2020 | Livingston FC | - | St. Mirren FC | 0:1 | ||||
| 16. Round | 05/12/2020 | Livingston FC | - | Dundee United | 2:0 | ||||
| 17. Round | 12/12/2020 | St. Johnstone FC | - | Livingston FC | 1:2 | ||||
| 19. Round | 23/12/2020 | Hamilton Academical | - | Livingston FC | 0:2 | ||||
| 20. Round | 26/12/2020 | Kilmarnock FC | - | Livingston FC | 1:2 | ||||
| 22. Round | 02/01/2021 | Hibernian FC | - | Livingston FC | 0:3 | ||||
| 23. Round | 10/01/2021 | Livingston FC | - | Ross County FC | 3:1 | ||||
| 24. Round | 16/01/2021 | Celtic FC | - | Livingston FC | 0:0 | ||||
| 26. Round | 27/01/2021 | Livingston FC | - | Kilmarnock FC | 2:0 | ||||
| 21. Round | 30/01/2021 | Livingston FC | - | Aberdeen FC | 0:0 | ||||
| 27. Round | 02/02/2021 | Aberdeen FC | - | Livingston FC | 0:2 | ||||
| 28. Round | 06/02/2021 | Livingston FC | - | St. Johnstone FC | 1:2 | ||||
| 29. Round | 13/02/2021 | Dundee United | - | Livingston FC | 3:0 | ||||
| 30. Round | 03/03/2021 | Livingston FC | - | Rangers FC | 0:1 |  |
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