| 7. Round | 10/08/2019 | FK Torpedo Armavir | - | FK Chayka | 2:1 |  |
|||
| 8. Round | 14/08/2019 | Luch Vladivostok | - | FK Chayka | 1:1 | ||||
| 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 | ||||
| 17. Round | 12/10/2019 | Shinnik Yaroslavl | - | FK Chayka | 2:3 | ||||
| 19. Round | 23/10/2019 | Torpedo Moskva | - | FK Chayka | 2:1 | ||||
| 20. Round | 27/10/2019 | FK Chayka | - | Fakel Voronezh | 0:1 | ||||
| 21. Round | 03/11/2019 | FK Chayka | - | Baltika Kaliningrad | 1:0 | ||||
| 22. Round | 09/11/2019 | SKA-Khabarovsk | - | FK Chayka | 3:2 | ||||
| 23. Round | 13/11/2019 | FK Chayka | - | Mordovia Saransk | 3:1 | ||||
| 24. Round | 17/11/2019 | FK Nizhny Novgorod | - | FK Chayka | 1:2 |
Russia