| 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 | 2021/02/27 12:00 | FK Kyustendil v Levski Chepintsi | W | 2-1 |
| Europe Friendlies | 2021/01/30 12:00 | Septemvri Simitli v FK Kyustendil | W | 1-2 |
| Bulgaria Third League | 2020/11/14 12:00 | Chavdar Etropole v FK Kyustendil | L | 1-0 |
| Bulgaria Amateur Cup | 2021/09/29 14:00 | Rakitin Trudovets v OFK Kostinbrod | W | 3-4 |
| Bulgaria Third League | 2021/08/31 15:00 | Balkan Botevgrad v OFK Kostinbrod | L | 3-2 |
| Bulgaria Third League | 2021/08/18 15:00 | Granit Vladaya v OFK Kostinbrod | W | 0-2 |