| 1. Round | 15/02/2020 | Deportivo Maldonado | - | Boston River | 1:2 |  |
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| 2. Round | 23/02/2020 | Liverpool | - | Deportivo Maldonado | 1:1 |  |
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| 4. Round | 09/08/2020 | Deportivo Maldonado | - | Cerro Largo | 1:1 | ||||
| 7. Round | 22/08/2020 | River Plate | - | Deportivo Maldonado | 0:1 | |
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| 8. Round | 26/08/2020 | Deportivo Maldonado | - | Montevideo City Torque | 0:3 | ||||
| 9. Round | 29/08/2020 | Plaza Colonia | - | Deportivo Maldonado | 1:2 | ||||
| 10. Round | 06/09/2020 | Deportivo Maldonado | - | Progreso | 1:0 | ||||
| 12. Round | 13/09/2020 | Deportivo Maldonado | - | CA Cerro | 1:0 |  |
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| 13. Round | 19/09/2020 | Defensor Sporting | - | Deportivo Maldonado | 4:2 | |
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| 14. Round | 06/10/2020 | Deportivo Maldonado | - | Danubio | 0:0 | ||||
| 15. Round | 11/10/2020 | Nacional | - | Deportivo Maldonado | 1:1 | |
Uruguay