| 1. Round | 15/05/2021 | Montevideo Wanderers | - | Boston River | 1:0 | ||||
| 2. Round | 22/05/2021 | Boston River | - | Rentistas | 1:2 | ||||
| 3. Round | 30/05/2021 | Peñarol | - | Boston River | 5:2 |  |
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| 4. Round | 06/06/2021 | Boston River | - | Montevideo City Torque | 1:2 | ||||
| 10. Round | 11/07/2021 | Boston River | - | Cerro Largo | 1:0 | ||||
| 11. Round | 16/07/2021 | Progreso | - | Boston River | 1:0 | ||||
| 15. Round | 21/08/2021 | Deportivo Maldonado | - | Boston River | 0:2 |  |
Uruguay