| 1. Round | 20/08/2023 | Boston River | - | Racing | 1:0 | ||||
| 2. Round | 27/08/2023 | CA Cerro | - | Boston River | 1:2 |  |
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| 3. Round | 02/09/2023 | Boston River | - | Peñarol | 0:1 |  |
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| 4. Round | 08/10/2023 | Boston River | - | Deportivo Maldonado | 2:0 | ||||
| 5. Round | 15/10/2023 | River Plate | - | Boston River | 2:1 | ||||
| 6. Round | 20/10/2023 | Boston River | - | Nacional | 2:0 | |
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| 7. Round | 24/10/2023 | Danubio | - | Boston River | 1:1 | ||||
| 8. Round | 04/11/2023 | Boston River | - | Fénix | 1:1 | |
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| 9. Round | 12/11/2023 | Montevideo Wanderers | - | Boston River | 0:2 | ||||
| 10. Round | 16/11/2023 | Boston River | - | La Luz | 1:2 | |
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| 11. Round | 20/11/2023 | Defensor Sporting | - | Boston River | 2:0 | ||||
| 12. Round | 24/11/2023 | Boston River | - | Montevideo City Torque | 2:0 | ||||
| 13. Round | 29/11/2023 | Liverpool | - | Boston River | 2:0 | ||||
| 15. Round | 08/12/2023 | Plaza Colonia | - | Boston River | 3:2 | |
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