| 2. Round | 20/07/2019 | CSKA Moskva | - | FK Orenburg | 2:1 | ||||
| 3. Round | 28/07/2019 | FK Orenburg | - | Zenit St. Petersburg | 0:2 | ||||
| 4. Round | 05/08/2019 | Akhmat Grozny | - | FK Orenburg | 2:1 | ||||
| 5. Round | 10/08/2019 | FK Orenburg | - | FK Tambov | 2:2 | ||||
| 6. Round | 16/08/2019 | FK Orenburg | - | FK Sochi | 1:1 | ||||
| 7. Round | 25/08/2019 | Arsenal Tula | - | FK Orenburg | 2:1 | ||||
| 10. Round | 22/09/2019 | FK Orenburg | - | Lokomotiv Moskva | 2:3 | ||||
| 13. Round | 20/10/2019 | FK Orenburg | - | Krylia Sovetov | 0:1 | ||||
| 19. Round | 07/12/2019 | FK Tambov | - | FK Orenburg | 3:0 | ||||
| 20. Round | 28/02/2020 | Krylia Sovetov | - | FK Orenburg | 1:1 | ||||
| 18. Round | 11/03/2020 | FK Sochi | - | FK Orenburg | 5:1 | ||||
| 23. Round | 21/06/2020 | Lokomotiv Moskva | - | FK Orenburg | 1:0 | ||||
| 26. Round | 05/07/2020 | Rubin Kazan | - | FK Orenburg | 1:0 | ||||
| 27. Round | 08/07/2020 | FK Orenburg | - | CSKA Moskva | 0:4 | ||||
| 28. Round | 12/07/2020 | FK Orenburg | - | FK Rostov | 0:0 | ||||
| 29. Round | 15/07/2020 | Zenit St. Petersburg | - | FK Orenburg | 4:1 | ||||
| 30. Round | 22/07/2020 | Dinamo Moskva | - | FK Orenburg | 0:1 |
Italy