| 1. Round | 30/07/2023 | Lokomotiv Moskva [U16] | - | Chertanovo Football Academy [U16] | 3:1 | ||||
| 2. Round | 06/08/2023 | Chertanovo Football Academy [U16] | - | FShM Moskva [U16] | 4:0 | ||||
| 3. Round | 12/08/2023 | FK Rostov [U16] | - | Chertanovo Football Academy [U16] | 2:0 | ||||
| 4. Round | 19/08/2023 | Chertanovo Football Academy [U16] | - | FK Krasnodar [U16] | 1:2 | ||||
| 6. Round | 09/09/2023 | FK Strogino Moskva [U16] | - | Chertanovo Football Academy [U16] | 0:1 | ||||
| 7. Round | 17/09/2023 | Uor-5 Egorievsk [U16] | - | Chertanovo Football Academy [U16] | 1:1 | ||||
| 8. Round | 24/09/2023 | Chertanovo Football Academy [U16] | - | Zenit St. Petersburg [U16] | 0:3 | ||||
| 9. Round | 30/09/2023 | Akademiya Konopleva [U16] | - | Chertanovo Football Academy [U16] | 1:1 | ||||
| 10. Round | 07/10/2023 | SShOR Zenit [U16] | - | Chertanovo Football Academy [U16] | 3:0 | ||||
| 11. Round | 22/10/2023 | Chertanovo Football Academy [U16] | - | Dinamo Moskva [U16] | 2:3 | ||||
| 12. Round | 28/10/2023 | Chertanovo Football Academy [U16] | - | Rubin Kazan [U16] | 0:2 | ||||
| 13. Round | 04/11/2023 | CSKA Moskva [U16] | - | Chertanovo Football Academy [U16] | 2:1 |
Russia