| 3. Round | 07/03/2020 | Rentistas | - | Deportivo Maldonado | 4:1 |  |
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| 5. Round | 15/08/2020 | Montevideo Wanderers | - | Deportivo Maldonado | 2:2 | ||||
| 7. Round | 22/08/2020 | River Plate | - | Deportivo Maldonado | 0:1 | ||||
| 8. Round | 26/08/2020 | Deportivo Maldonado | - | Montevideo City Torque | 0:3 | ||||
| 9. Round | 29/08/2020 | Plaza Colonia | - | Deportivo Maldonado | 1:2 | ||||
| 11. Round | 10/09/2020 | Fénix | - | Deportivo Maldonado | 1:0 | ||||
| 13. Round | 19/09/2020 | Defensor Sporting | - | Deportivo Maldonado | 4:2 |
Uruguay