| 1. Round | 20/08/2023 | Boston River | - | Racing | 1:0 |  |
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| 2. Round | 27/08/2023 | CA Cerro | - | Boston River | 1:2 | ||||
| 3. Round | 02/09/2023 | Boston River | - | Peñarol | 0:1 | ||||
| 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 | ||||
| 7. Round | 24/10/2023 | Danubio | - | Boston River | 1:1 |
Uruguay