| Bulgaria Third League | 2022/03/12 13:00 | Pirin Gotse Delchev v FK Kyustendil | L | 1-0 |
| Bulgaria Amateur Cup | 2021/11/17 12:00 | FK Kyustendil v FK Vitosha | L | 3-5 |
| Bulgaria Third League | 2021/10/06 13:00 | FK Kyustendil v OFK Kostinbrod | W | 3-2 |
| Bulgaria Third League | 2021/08/07 16:30 | FK Vitosha Bistrica v FK Kyustendil | D | 2-2 |
| Bulgaria Third League | 2021/05/15 15:00 | FK Kyustendil v Chavdar Etropole | W | 2-0 |
| Bulgaria Third League | 2021/05/12 15:00 | Rilski Sportist v FK Kyustendil | W | 0-1 |
| Bulgaria Third League | 2021/04/28 13:00 | FK Velbazhd v FK Kyustendil | W | 0-3 |
| Bulgaria Third League | 2021/03/20 13:00 | FK Kyustendil v Belasitsa | D | 1-1 |
| Bulgaria Third League | 2021/11/10 12:00 | Pirin 2002 v PFC Pirin Blagoevgrad II | L | 2-0 |
| Bulgaria Third League | 2021/10/06 13:00 | Belasitsa v PFC Pirin Blagoevgrad II | L | 3-1 |
| Bulgaria Amateur Cup | 2021/09/15 13:00 | PFC Pirin Blagoevgrad II v Vihren Sandanski | L | 1-2 |
| Bulgaria Third League | 2021/08/29 15:00 | FK Hebar Pazarzhik II v PFC Pirin Blagoevgrad II | D | 2-2 |
| Bulgaria Amateur Cup | 2020/09/23 13:00 | PFC Pirin Blagoevgrad II v Belasitsa | L | 0-2 |