| 1. Round | 15/02/2020 | Deportivo Maldonado | - | Boston River | 1:2 | ||||
| 2. Round | 23/02/2020 | Liverpool | - | Deportivo Maldonado | 1:1 | ||||
| 3. Round | 07/03/2020 | Rentistas | - | Deportivo Maldonado | 4:1 |  |
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| 4. Round | 09/08/2020 | Deportivo Maldonado | - | Cerro Largo | 1:1 | ||||
| 5. Round | 15/08/2020 | Montevideo Wanderers | - | Deportivo Maldonado | 2:2 | ||||
| 8. Round | 26/08/2020 | Deportivo Maldonado | - | Montevideo City Torque | 0:3 | ||||
| 9. Round | 29/08/2020 | Plaza Colonia | - | Deportivo Maldonado | 1:2 |
Uruguay