| 4. Round | 05/08/2019 | Akhmat Grozny [U20] | - | FK Orenburg [U20] | 2:1 | ||||
| 9. Round | 14/09/2019 | FK Orenburg [U20] | - | Rubin Kazan [U20] | 0:1 | ||||
| 10. Round | 21/09/2019 | FK Orenburg [U20] | - | Lokomotiv Moskva [U20] | 1:2 | ||||
| 11. Round | 28/09/2019 | Spartak Moskva [U20] | - | FK Orenburg [U20] | 1:0 | ||||
| 12. Round | 04/10/2019 | FK Orenburg [U20] | - | Dinamo Moskva [U20] | 1:3 | ||||
| 13. Round | 19/10/2019 | FK Orenburg [U20] | - | Krylia Sovetov [U20] | 0:1 |  |
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| 14. Round | 27/10/2019 | FK Krasnodar [U20] | - | FK Orenburg [U20] | 0:1 | ||||
| 15. Round | 03/11/2019 | FK Ural [U20] | - | FK Orenburg [U20] | 1:1 | ||||
| 16. Round | 09/11/2019 | FK Orenburg [U20] | - | FK Ufa [U20] | 3:0 | |
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| 17. Round | 22/11/2019 | FK Orenburg [U20] | - | Akhmat Grozny [U20] | 3:1 | |
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| 18. Round | 30/11/2019 | FK Sochi [U20] | - | FK Orenburg [U20] | 3:1 | |
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| 20. Round | 29/02/2020 | Krylia Sovetov [U20] | - | FK Orenburg [U20] | 3:1 | |
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| 21. Round | 06/03/2020 | FK Orenburg [U20] | - | Arsenal Tula [U20] | 1:5 | ||||
| 22. Round | 13/03/2020 | FK Orenburg [U20] | - | Spartak Moskva [U20] | 0:4 |
Russia