| 1. Round | 18/01/2021 | Boston River | - | Deportivo Maldonado | 5:0 | ||||
| 2. Round | 21/01/2021 | Deportivo Maldonado | - | Liverpool | 2:4 | ||||
| 6. Round | 11/02/2021 | Peñarol | - | Deportivo Maldonado | 1:1 | ||||
| 7. Round | 14/02/2021 | Deportivo Maldonado | - | River Plate | 1:2 | ||||
| 8. Round | 18/02/2021 | Montevideo City Torque | - | Deportivo Maldonado | 1:1 | ||||
| 12. Round | 13/03/2021 | CA Cerro | - | Deportivo Maldonado | 2:3 | ||||
| 13. Round | 18/03/2021 | Deportivo Maldonado | - | Defensor Sporting | 2:1 |  |
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| 14. Round | 23/03/2021 | Danubio | - | Deportivo Maldonado | 2:2 |
Uruguay