| Bulgaria Third League | 2023/08/19 15:00 | Septemvri Sofia II v FK Kyustendil | L | 1-0 |
| Bulgaria Third League | 2024/02/24 12:00 | FK Kyustendil v CSKA 1948 III | D | 0-0 |
| Bulgaria Third League | 2024/02/17 12:00 | Balkan Botevgrad v FK Kyustendil | L | 4-1 |
| Bulgaria Third League | 2023/11/11 12:00 | FK Vitosha Bistrica v FK Kyustendil | L | 2-1 |
| Bulgaria Third League | 2023/10/26 13:00 | Slavia Sofia II v FK Kyustendil | W | 1-4 |
| Bulgaria Third League | 2023/10/14 13:00 | Pirin 2002 v FK Kyustendil | W | 2-4 |
| Bulgaria Third League | 2023/09/20 14:00 | FK Kyustendil v Vihren Sandanski | L | 1-2 |
| Bulgaria Third League | 2023/09/15 14:00 | Botev Ihtiman v FK Kyustendil | W | 1-2 |
| Bulgarien - Cup | 2023/09/05 13:00 | FK Kyustendil v Dunav Ruse | L | 3-5 |
| Bulgaria Third League | 2024/02/24 12:00 | Minyor Pernik v Septemvri Sofia II | L | 1-0 |
| Bulgaria Third League | 2024/02/10 12:00 | Slivnishki Geroy v Septemvri Sofia II | L | 2-1 |
| Bulgaria Third League | 2023/12/02 12:00 | Septemvri Sofia II v Chavdar Etropole | L | 0-1 |
| Bulgaria Third League | 2023/11/18 12:00 | Septemvri Sofia II v CSKA 1948 III | W | 2-0 |
| Bulgaria Third League | 2023/11/03 12:00 | Septemvri Sofia II v PFC Levski Sofia II | D | 1-1 |
| Bulgaria Third League | 2023/10/14 13:00 | CSKA Sofia II v Septemvri Sofia II | L | 2-1 |
| Bulgaria Third League | 2023/10/07 13:00 | Septemvri Sofia II v Slavia Sofia II | D | 1-1 |
| Bulgaria Third League | 2023/09/23 14:00 | Septemvri Sofia II v Pirin 2002 | W | 3-0 |