| 1. Round | 07/07/2019 | Baltika Kaliningrad | - | Spartak Moskva 2 | 0:1 | ||||
| 2. Round | 13/07/2019 | Torpedo Moskva | - | Baltika Kaliningrad | 2:0 | ||||
| 3. Round | 20/07/2019 | Baltika Kaliningrad | - | FK Chayka | 0:1 | ||||
| 5. Round | 28/07/2019 | Baltika Kaliningrad | - | FK Chertanovo | 1:2 | ||||
| 6. Round | 03/08/2019 | SKA-Khabarovsk | - | Baltika Kaliningrad | 2:0 | ||||
| 7. Round | 10/08/2019 | Mordovia Saransk | - | Baltika Kaliningrad | 0:3 | ||||
| 8. Round | 14/08/2019 | Baltika Kaliningrad | - | FK Nizhny Novgorod | 2:1 | ||||
| 9. Round | 18/08/2019 | FK Torpedo Armavir | - | Baltika Kaliningrad | 1:1 | ||||
| 10. Round | 25/08/2019 | Baltika Kaliningrad | - | Luch Vladivostok | 0:0 | ||||
| 11. Round | 31/08/2019 | Avangard Kursk | - | Baltika Kaliningrad | 0:0 |  |
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| 12. Round | 08/09/2019 | Tekstilshchik Ivanovo | - | Baltika Kaliningrad | 1:5 | ||||
| 24. Round | 17/11/2019 | Baltika Kaliningrad | - | SKA-Khabarovsk | 1:0 | |
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| 25. Round | 23/11/2019 | Baltika Kaliningrad | - | Mordovia Saransk | 0:2 | ||||
| 26. Round | 09/03/2020 | FK Nizhny Novgorod | - | Baltika Kaliningrad | 0:0 | ||||
| 27. Round | 15/03/2020 | Baltika Kaliningrad | - | FK Torpedo Armavir | 2:0 |
Russia