| 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 | ||||
| 4. Round | 06/06/2021 | Boston River | - | Montevideo City Torque | 1:2 | ||||
| 5. Round | 14/06/2021 | Villa Española | - | Boston River | 2:2 | ||||
| 6. Round | 19/06/2021 | Boston River | - | Nacional | 1:1 |  |
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| 7. Round | 22/06/2021 | Cerrito | - | Boston River | 1:0 | ||||
| 8. Round | 27/06/2021 | Boston River | - | Liverpool | 1:1 | ||||
| 12. Round | 31/07/2021 | Boston River | - | Sud América | 2:0 | ||||
| 13. Round | 09/08/2021 | Plaza Colonia | - | Boston River | 0:0 | ||||
| 14. Round | 16/08/2021 | Boston River | - | Fénix | 0:2 | ||||
| 15. Round | 21/08/2021 | Deportivo Maldonado | - | Boston River | 0:2 |
Uruguay