1. Round | 13/07/2019 | FK Rostov | - | FK Orenburg | 2:1 | ||||
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 | ||||
17. Round | 23/11/2019 | FK Orenburg | - | Akhmat Grozny | 1:2 | ||||
20. Round | 28/02/2020 | Krylia Sovetov | - | FK Orenburg | 1:1 |