| 14. Round | 24/11/2019 | Hamilton Academical | - | Rangers FC | 1:3 | ||||
| 15. Round | 30/11/2019 | Livingston FC | - | Hamilton Academical | 0:0 | ||||
| 16. Round | 04/12/2019 | Celtic FC | - | Hamilton Academical | 2:1 | ||||
| 17. Round | 07/12/2019 | Hamilton Academical | - | St. Mirren FC | 0:1 | ||||
| 18. Round | 14/12/2019 | Aberdeen FC | - | Hamilton Academical | 1:0 | ||||
| 19. Round | 21/12/2019 | Hamilton Academical | - | Heart of Midlothian | 2:1 | ||||
| 20. Round | 26/12/2019 | Hamilton Academical | - | St. Johnstone FC | 0:1 | ||||
| 21. Round | 29/12/2019 | Motherwell FC | - | Hamilton Academical | 1:2 | ||||
| 24. Round | 02/02/2020 | Hamilton Academical | - | Celtic FC | 1:4 | ||||
| 25. Round | 05/02/2020 | St. Mirren FC | - | Hamilton Academical | 1:1 | ||||
| 26. Round | 11/02/2020 | Hamilton Academical | - | Aberdeen FC | 1:3 | ||||
| 27. Round | 15/02/2020 | Heart of Midlothian | - | Hamilton Academical | 2:2 | ||||
| 28. Round | 22/02/2020 | Hamilton Academical | - | Motherwell FC | 0:0 | ||||
| 29. Round | 04/03/2020 | Rangers FC | - | Hamilton Academical | 0:1 | ||||
| 30. Round | 07/03/2020 | Hamilton Academical | - | Kilmarnock FC | 1:0 |
England