| 1. Round | 07/07/2019 | FK Chayka | - | FK Chertanovo | 0:1 | ||||
| 2. Round | 13/07/2019 | FK Chertanovo | - | Enisey Krasnoyarsk | 2:1 | ||||
| 3. Round | 20/07/2019 | Fakel Voronezh | - | FK Chertanovo | 0:0 | ||||
| 4. Round | 24/07/2019 | FK Chertanovo | - | Rotor Volgograd | 1:0 |  |
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| 5. Round | 28/07/2019 | Baltika Kaliningrad | - | FK Chertanovo | 1:2 | ||||
| 6. Round | 03/08/2019 | FK Chertanovo | - | FK Khimki | 0:0 | ||||
| 7. Round | 10/08/2019 | SKA-Khabarovsk | - | FK Chertanovo | 0:0 | ||||
| 8. Round | 14/08/2019 | FK Chertanovo | - | FK Krasnodar 2 | 1:2 | ||||
| 9. Round | 18/08/2019 | Mordovia Saransk | - | FK Chertanovo | 2:3 | ||||
| 10. Round | 25/08/2019 | FK Chertanovo | - | FK Tom Tomsk | 1:1 |  |
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| 11. Round | 31/08/2019 | FK Nizhny Novgorod | - | FK Chertanovo | 0:0 | ||||
| 12. Round | 07/09/2019 | FK Chertanovo | - | FK Neftekhimik | 2:2 | ||||
| 13. Round | 15/09/2019 | FK Torpedo Armavir | - | FK Chertanovo | 1:1 | ||||
| 26. Round | 10/03/2020 | FK Krasnodar 2 | - | FK Chertanovo | 1:2 | ||||
| 27. Round | 15/03/2020 | FK Chertanovo | - | Mordovia Saransk | 3:0 |
Belarus