| Bulgaria Third League | 2020/09/19 14:00 | Nadezhda Dobroslavci v Pirin Gotse Delchev | L | 2-4 |
| Europe Friendlies | 2020/01/18 11:00 | Maritsa Plovdiv v Nadezhda Dobroslavci | L | 4-1 |
| Bulgaria Third League | 2019/11/06 12:00 | FK Bansko v Nadezhda Dobroslavci | L | 5-1 |
| Bulgaria Third League | 2019/06/01 15:00 | Nadezhda Dobroslavci v Pirin 2002 | L | 0-4 |
| Bulgaria Third League | 2019/05/18 15:00 | Nadezhda Dobroslavci v Marek Dupnitsa | D | 1-1 |
| Bulgaria Third League | 2019/05/11 15:00 | Vihren Sandanski v Nadezhda Dobroslavci | L | 2-0 |
| Bulgaria Third League | 2019/05/04 15:00 | Nadezhda Dobroslavci v Oborishte | W | 2-1 |
| Bulgaria Third League | 2019/04/24 13:00 | FK Velbazhd v Nadezhda Dobroslavci | W | 1-4 |
| 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 | 2019/11/06 12:00 | Minyor Pernik v FK Kyustendil | L | 4-0 |
| Europe Friendlies | 2019/07/24 15:00 | FK Kyustendil v Minyor Pernik | W | 3-1 |