| Bulgaria Third League | 2020/10/17 13:00 | Nadezhda Dobroslavci v FK Kyustendil | W | 0-2 |
| Bulgaria Third League | 2022/04/09 14:00 | FK Bansko v FK Kyustendil | D | 0-0 |
| Bulgaria Third League | 2022/03/23 13:00 | FK Kyustendil v PFC Pirin Blagoevgrad II | W | 2-0 |
| 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 | 2022/02/26 12:00 | Granit Vladaya v Nadezhda Dobroslavci | W | 0-2 |
| Bulgaria Third League | 2021/11/10 12:00 | Nadezhda Dobroslavci v Oborishte | D | 1-1 |
| Bulgaria Amateur Cup | 2021/10/13 13:00 | Levski Chepintsi v Nadezhda Dobroslavci | W | 0-4 |
| Bulgaria Third League | 2021/10/06 13:00 | Botev Ihtiman v Nadezhda Dobroslavci | L | 4-0 |
| Bulgaria Cup | 2021/09/07 13:00 | Nadezhda Dobroslavci v Spartak Varna | L | 0-3 |
| Bulgaria Third League | 2021/09/04 15:00 | Nadezhda Dobroslavci v Pirin 2002 | D | 1-1 |
| Bulgaria Third League | 2021/08/14 15:00 | Nadezhda Dobroslavci v Granit Vladaya | L | 0-3 |
| World Club Friendlies | 2021/07/10 07:00 | Lokomotiv 1929 Sofia v Nadezhda Dobroslavci | L | 2-1 |