| 1. Round | 07/07/2019 | FK Chayka | - | FK Chertanovo | 0:1 | ||||
| 2. Round | 13/07/2019 | Fakel Voronezh | - | FK Chayka | 0:0 | ||||
| 3. Round | 20/07/2019 | Baltika Kaliningrad | - | FK Chayka | 0:1 |  |
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| 4. Round | 24/07/2019 | FK Chayka | - | SKA-Khabarovsk | 0:2 | ||||
| 5. Round | 28/07/2019 | Mordovia Saransk | - | FK Chayka | 0:0 | ||||
| 6. Round | 03/08/2019 | FK Chayka | - | FK Nizhny Novgorod | 0:0 | ||||
| 7. Round | 10/08/2019 | FK Torpedo Armavir | - | FK Chayka | 2:1 | ||||
| 8. Round | 14/08/2019 | Luch Vladivostok | - | FK Chayka | 1:1 | ||||
| 9. Round | 18/08/2019 | Avangard Kursk | - | FK Chayka | 1:1 | ||||
| 10. Round | 25/08/2019 | FK Chayka | - | Tekstilshchik Ivanovo | 3:0 | ||||
| 11. Round | 31/08/2019 | Enisey Krasnoyarsk | - | FK Chayka | 1:3 | ||||
| 12. Round | 07/09/2019 | FK Chayka | - | Rotor Volgograd | 2:1 | ||||
| 13. Round | 14/09/2019 | FK Khimki | - | FK Chayka | 1:0 | ||||
| 14. Round | 21/09/2019 | FK Chayka | - | FK Krasnodar 2 | 1:1 | ||||
| 15. Round | 29/09/2019 | FK Tom Tomsk | - | FK Chayka | 3:1 | ||||
| 16. Round | 05/10/2019 | FK Chayka | - | FK Neftekhimik | 0:2 |
Russia