| 1. Round | 07/07/2023 | FK Chertanovo [U20] | - | FK Orenburg [U20] | 5:1 | ||||
| 2. Round | 14/07/2023 | FK Orenburg [U20] | - | Zenit St. Petersburg [U20] | 1:4 |  |
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| 3. Round | 21/07/2023 | Akademiya Konopleva [U20] | - | FK Orenburg [U20] | 0:2 | ||||
| 4. Round | 28/07/2023 | Baltika Kaliningrad [U20] | - | FK Orenburg [U20] | 2:2 | |
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| 5. Round | 04/08/2023 | FK Orenburg [U20] | - | Lokomotiv Moskva [U20] | 0:5 | ||||
| 6. Round | 11/08/2023 | Krylia Sovetov [U20] | - | FK Orenburg [U20] | 2:1 | |
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| 7. Round | 18/08/2023 | FK Orenburg [U20] | - | FK Sochi [U20] | 0:5 | ||||
| 8. Round | 25/08/2023 | Spartak Moskva [U20] | - | FK Orenburg [U20] | 8:0 | |
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| 10. Round | 15/09/2023 | FK Ural [U20] | - | FK Orenburg [U20] | 2:0 | |
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| 11. Round | 22/09/2023 | FK Orenburg [U20] | - | CSKA Moskva [U20] | 2:1 | ||||
| 12. Round | 29/09/2023 | Fakel Voronezh [U20] | - | FK Orenburg [U20] | 0:0 | |
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| 13. Round | 06/10/2023 | FK Orenburg [U20] | - | Rubin Kazan [U20] | 0:4 | ||||
| 14. Round | 20/10/2023 | FK Krasnodar [U20] | - | FK Orenburg [U20] | 5:0 | ||||
| 17. Round | 10/11/2023 | FK Orenburg [U20] | - | Akhmat Grozny [U20] | 0:0 | ||||
| 19. Round | 01/12/2023 | FK Orenburg [U20] | - | Uor-5 Egorievsk [U20] | 1:6 |
Russia