| 4. Round | 01/09/2018 | Hamilton Academical | - | St. Johnstone FC | 1:2 | ||||
| 5. Round | 15/09/2018 | Livingston FC | - | Hamilton Academical | 1:0 | ||||
| 17. Round | 08/12/2018 | Hamilton Academical | - | Hibernian FC | 0:1 | ||||
| 18. Round | 16/12/2018 | Rangers FC | - | Hamilton Academical | 1:0 | ||||
| 19. Round | 22/12/2018 | Hamilton Academical | - | Kilmarnock FC | 1:1 | ||||
| 20. Round | 26/12/2018 | Heart of Midlothian | - | Hamilton Academical | 2:0 | ||||
| 21. Round | 29/12/2018 | Hamilton Academical | - | Motherwell FC | 1:2 | ||||
| 23. Round | 26/01/2019 | Celtic FC | - | Hamilton Academical | 3:0 |  |
|||
| 25. Round | 06/02/2019 | Hamilton Academical | - | St. Johnstone FC | 2:1 | ||||
| 26. Round | 16/02/2019 | Hibernian FC | - | Hamilton Academical | 2:0 | |
|||
| 27. Round | 24/02/2019 | Hamilton Academical | - | Rangers FC | 0:5 | ||||
| 28. Round | 27/02/2019 | Aberdeen FC | - | Hamilton Academical | 0:2 | ||||
| 29. Round | 09/03/2019 | Motherwell FC | - | Hamilton Academical | 3:0 | |
|||
| 30. Round | 16/03/2019 | Hamilton Academical | - | Heart of Midlothian | 1:0 | ||||
| 31. Round | 30/03/2019 | Kilmarnock FC | - | Hamilton Academical | 5:0 |
Germany
Ghana