1. Round | 03/08/2019 | Ross County FC | - | Hamilton Academical | 3:0 | ||||
4. Round | 31/08/2019 | Heart of Midlothian | - | Hamilton Academical | 2:2 | ||||
5. Round | 14/09/2019 | Hamilton Academical | - | Celtic FC | 0:1 | ||||
8. Round | 06/10/2019 | Rangers FC | - | Hamilton Academical | 5:0 | ||||
13. Round | 09/11/2019 | Kilmarnock FC | - | Hamilton Academical | 2:2 | ||||
22. Round | 22/01/2020 | Hibernian FC | - | Hamilton Academical | 2:1 | ||||
23. Round | 25/01/2020 | Hamilton Academical | - | Livingston FC | 2:4 |