| 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 Third League | 2020/10/17 13:00 | Nadezhda Dobroslavci v FK Kyustendil | W | 0-2 |
| Bulgaria Amateur Cup | 2020/09/23 14:00 | Marek Dupnitsa v FK Kyustendil | L | 3-0 |
| Bulgaria Third League | 2020/09/19 14:00 | Pirin 2002 v FK Kyustendil | W | 0-3 |
| Bulgaria Third League | 2020/09/05 14:00 | Belasitsa v FK Kyustendil | L | 1-0 |
| Club Friendly List | 2020/02/14 12:00 | FK Kyustendil v Septemvri Simitli | W | 2-0 |
| Europe Friendlies | 2020/01/25 12:00 | FK Kyustendil v Marek Dupnitsa | L | 2-3 |
| Bulgaria Third League | 2021/02/24 12:00 | Marek Dupnitsa v Levski Chepintsi | L | 6-0 |
| Bulgaria Third League | 2020/10/24 13:00 | Levski Chepintsi v Perun Kresna | D | 3-3 |
| Bulgaria Third League | 2020/09/26 14:00 | Levski Chepintsi v Balkan Botevgrad | W | 2-1 |
| Bulgaria Third League | 2020/09/19 14:00 | Slivnishki Geroy v Levski Chepintsi | L | 1-0 |
| Bulgaria Third League | 2020/08/29 15:00 | Levski Chepintsi v Belasitsa | L | 1-3 |