| Russia Regional League | 2019/06/09 13:00 | FC Progress Chernyakhovsk v FK Krasnaya Zvezda Sovetsk | L | 2-1 |
| Russia Regional League | 2019/08/17 13:00 | Guryevsk v FK Olimpia Gvardejsk | W | 1-3 |
| Russia Regional League | 2019/06/30 13:00 | FK Olimpia Gvardejsk v FC Svetlyi | W | 5-4 |
| Russia Regional League | 2019/06/22 15:00 | FK Kantiana v FK Olimpia Gvardejsk | W | 2-4 |
| Russia Regional League | 2019/06/12 13:00 | FK Shtorm v FK Olimpia Gvardejsk | W | 0-3 |
| Russia Regional League | 2019/06/02 13:00 | FK Olimpia Gvardejsk v Baltika-M Kaliningrad | L | 1-3 |
| Russia Regional League | 2019/05/12 13:00 | FK Olimpia Gvardejsk v FC Kaliningrad 2018 | W | 3-1 |
| Russian Matches | 2018/07/29 13:00 | FK Kantiana v FK Olimpia Gvardejsk | W | 0-3 |