| Bulgaria Third League | 2021/10/06 13:00 | FK Kyustendil v OFK Kostinbrod | L | 3-2 |
| Bulgaria Third League | 2022/04/16 14:00 | Vihren Sandanski v OFK Kostinbrod | D | 1-1 |
| Bulgaria Third League | 2022/03/26 13:00 | OFK Kostinbrod v Pirin 2002 | D | 3-3 |
| Bulgaria Third League | 2022/03/23 13:00 | FK Vitosha Bistrica v OFK Kostinbrod | L | 3-0 |
| Bulgaria Third League | 2021/11/10 12:00 | OFK Kostinbrod v Slivnishki Geroy | L | 0-1 |
| Bulgaria Amateur Cup | 2021/10/13 13:00 | OFK Kostinbrod v Balkan Botevgrad | L | 0-1 |
| Bulgaria Third League | 2021/10/06 13:00 | FK Kyustendil v OFK Kostinbrod | L | 3-2 |
| 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 | 2022/04/16 14:00 | FK Kyustendil v Nadezhda Dobroslavci | W | 3-0 |
| 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 |