| 1. Round | 02/08/2020 | Celtic FC | - | Hamilton Academical | 5:1 | ||||
| 2. Round | 08/08/2020 | Hamilton Academical | - | Ross County 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 | ||||
| 8. Round | 19/09/2020 | Kilmarnock FC | - | Hamilton Academical | 2:1 | ||||
| 3. Round | 20/10/2020 | Aberdeen FC | - | Hamilton Academical | 4:2 | ||||
| 17. Round | 12/12/2020 | Hamilton Academical | - | Hibernian FC | 0:4 |  |
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| 20. Round | 26/12/2020 | Hamilton Academical | - | Celtic FC | 0:3 | ||||
| 22. Round | 02/01/2021 | Hamilton Academical | - | Motherwell FC | 3:0 | ||||
| 23. Round | 09/01/2021 | Kilmarnock FC | - | Hamilton Academical | 2:0 | ||||
| 28. Round | 07/02/2021 | Hamilton Academical | - | Rangers FC | 1:1 | ||||
| 29. Round | 13/02/2021 | Motherwell FC | - | Hamilton Academical | 1:4 | ||||
| 12. Round | 17/02/2021 | St. Mirren FC | - | Hamilton Academical | 1:1 | ||||
| 33. Round | 20/02/2021 | Hibernian FC | - | Hamilton Academical | 2:0 | ||||
| 30. Round | 03/03/2021 | Hamilton Academical | - | St. Johnstone FC | 1:1 |
Canada
Poland