| 2. Round | 20/07/2019 | CSKA Moskva [U20] | - | FK Orenburg [U20] | 2:0 | ||||
| 3. Round | 27/07/2019 | FK Orenburg [U20] | - | Zenit St. Petersburg [U20] | 0:1 | ||||
| 4. Round | 05/08/2019 | Akhmat Grozny [U20] | - | FK Orenburg [U20] | 2:1 | ||||
| 5. Round | 09/08/2019 | FK Orenburg [U20] | - | FK Tambov [U20] | 0:1 | ||||
| 6. Round | 15/08/2019 | FK Orenburg [U20] | - | FK Sochi [U20] | 2:1 | ||||
| 7. Round | 24/08/2019 | Arsenal Tula [U20] | - | FK Orenburg [U20] | 2:1 | ||||
| 8. Round | 30/08/2019 | FK Ufa [U20] | - | FK Orenburg [U20] | 1:1 | ||||
| 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 | ||||
| 12. Round | 04/10/2019 | FK Orenburg [U20] | - | Dinamo Moskva [U20] | 1:3 | ||||
| 19. Round | 06/12/2019 | FK Tambov [U20] | - | FK Orenburg [U20] | 3:2 |
Russia