| 1. Round | 01/08/2020 | Dundee United | - | St. Johnstone FC | 1:1 | ||||
| 2. Round | 08/08/2020 | Motherwell FC | - | Dundee United | 0:1 | ||||
| 3. Round | 11/08/2020 | Dundee United | - | Hibernian FC | 0:1 |  |
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| 4. Round | 15/08/2020 | Ross County FC | - | Dundee United | 1:2 | ||||
| 5. Round | 22/08/2020 | Dundee United | - | Celtic FC | 0:1 | ||||
| 6. Round | 29/08/2020 | Kilmarnock FC | - | Dundee United | 4:0 | ||||
| 7. Round | 12/09/2020 | Rangers FC | - | Dundee United | 4:0 | ||||
| 8. Round | 19/09/2020 | Dundee United | - | St. Mirren FC | 2:1 | ||||
| 9. Round | 26/09/2020 | Hamilton Academical | - | Dundee United | 1:1 | ||||
| 10. Round | 02/10/2020 | Dundee United | - | Livingston FC | 1:2 | ||||
| 11. Round | 17/10/2020 | Dundee United | - | Aberdeen FC | 0:0 | ||||
| 31. Round | 07/03/2021 | Dundee United | - | Celtic FC | 0:0 |
Scotland