| 4. Round | 15/08/2020 | Hamilton Academical | - | St. Mirren FC | 0:1 | ||||
| 5. Round | 22/08/2020 | Motherwell FC | - | Hamilton Academical | 0:1 | ||||
| 6. Round | 29/08/2020 | Hamilton Academical | - | Rangers FC | 0:2 | ||||
| 7. Round | 12/09/2020 | Livingston FC | - | Hamilton Academical | 1:2 |  |
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| 8. Round | 19/09/2020 | Kilmarnock FC | - | Hamilton Academical | 2:1 | |
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| 9. Round | 26/09/2020 | Hamilton Academical | - | Dundee United | 1:1 | ||||
| 3. Round | 20/10/2020 | Aberdeen FC | - | Hamilton Academical | 4:2 | ||||
| 14. Round | 08/11/2020 | Rangers FC | - | Hamilton Academical | 8:0 | ||||
| 19. Round | 23/12/2020 | Hamilton Academical | - | Livingston FC | 0:2 | ||||
| 20. Round | 26/12/2020 | Hamilton Academical | - | Celtic FC | 0:3 | ||||
| 26. Round | 27/01/2021 | Celtic FC | - | Hamilton Academical | 2:0 | ||||
| 27. Round | 03/02/2021 | Hamilton Academical | - | Ross County FC | 1:2 | ||||
| 33. Round | 20/02/2021 | Hibernian FC | - | Hamilton Academical | 2:0 |
Scotland