| 1. Round | 18/01/2021 | Boston River | - | Deportivo Maldonado | 5:0 | ||||
| 3. Round | 30/01/2021 | Deportivo Maldonado | - | Rentistas | 3:1 | ||||
| 4. Round | 02/02/2021 | Cerro Largo | - | Deportivo Maldonado | 1:2 |  |
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| 5. Round | 06/02/2021 | Deportivo Maldonado | - | Montevideo Wanderers | 1:1 | ||||
| 6. Round | 11/02/2021 | Peñarol | - | Deportivo Maldonado | 1:1 |  |
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| 8. Round | 18/02/2021 | Montevideo City Torque | - | Deportivo Maldonado | 1:1 | |
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| 9. Round | 22/02/2021 | Deportivo Maldonado | - | Plaza Colonia | 1:1 |
Uruguay