| 3. Round | 24/08/2019 | Hamilton Academical | - | Motherwell FC | 1:3 | ||||
| 4. Round | 31/08/2019 | Heart of Midlothian | - | Hamilton Academical | 2:2 |  |
|||
| 5. Round | 14/09/2019 | Hamilton Academical | - | Celtic FC | 0:1 | ||||
| 6. Round | 21/09/2019 | St. Mirren FC | - | Hamilton Academical | 0:0 | ||||
| 16. Round | 04/12/2019 | Celtic FC | - | Hamilton Academical | 2:1 | ||||
| 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 | ||||
| 22. Round | 22/01/2020 | Hibernian FC | - | Hamilton Academical | 2:1 | ||||
| 23. Round | 25/01/2020 | Hamilton Academical | - | Livingston FC | 2:4 | ||||
| 24. Round | 02/02/2020 | Hamilton Academical | - | Celtic FC | 1:4 | |
|||
| 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 | ||||
| 30. Round | 07/03/2020 | Hamilton Academical | - | Kilmarnock FC | 1:0 |
England