| 1. Round | 10/04/2021 | Hamilton Academical | - | Dundee United | 0:1 |  |
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| 2. Round | 21/04/2021 | Kilmarnock FC | - | Dundee United | 3:0 | ||||
| 3. Round | 01/05/2021 | Dundee United | - | Ross County FC | 0:2 | ||||
| 4. Round | 12/05/2021 | Dundee United | - | Motherwell FC | 2:2 | ||||
| 5. Round | 16/05/2021 | St. Mirren FC | - | Dundee United | 0:0 |  |
Scotland