Head to Head
| Bulgaria Third League | 2022/11/19 12:00 | Septemvri Simitli v FK Kyustendil | D | 1-1 |
| Europe Friendlies | 2021/01/30 12:00 | Septemvri Simitli v FK Kyustendil | L | 1-2 |
| Club Friendly List | 2020/02/14 12:00 | FK Kyustendil v Septemvri Simitli | L | 2-0 |
Home History
| Bulgaria Third League | 2023/08/26 15:00 | Septemvri Simitli v Vihren Sandanski | L | 1-2 |
| Bulgaria Third League | 2023/08/19 15:00 | Minyor Pernik v Septemvri Simitli | L | 4-1 |
| Bulgaria Third League | 2023/08/16 15:00 | Septemvri Simitli v Septemvri Sofia II | W | 2-0 |
| Bulgaria Third League | 2023/08/12 15:00 | Slivnishki Geroy v Septemvri Simitli | L | 2-1 |
| Bulgaria Third League | 2023/08/05 15:00 | Septemvri Simitli v CSKA 1948 III | L | 0-3 |
| Bulgaria Third League | 2023/05/14 15:00 | Septemvri Simitli v FK Bansko | W | 2-1 |
| Bulgaria Third League | 2023/04/12 14:00 | Septemvri Simitli v Balkan Botevgrad | W | 2-1 |
| Bulgaria Third League | 2023/03/25 13:00 | Septemvri Simitli v Slivnishki Geroy | L | 0-1 |
Away History
| Bulgaria Third League | 2023/08/26 15:00 | FK Kyustendil v Minyor Pernik | W | 2-0 |
| Bulgaria Third League | 2023/08/19 15:00 | Septemvri Sofia II v FK Kyustendil | L | 1-0 |
| Bulgaria Third League | 2023/08/16 15:00 | FK Kyustendil v Slivnishki Geroy | L | 0-1 |
| Bulgaria Third League | 2023/08/12 15:00 | CSKA 1948 III v FK Kyustendil | W | 0-3 |
| Bulgaria Third League | 2023/05/27 15:00 | FK Kyustendil v FK Bansko | W | 1-0 |
| Bulgaria Third League | 2023/04/12 14:00 | FK Kyustendil v Slivnishki Geroy | L | 0-2 |
| Bulgaria Third League | 2023/04/08 14:00 | Marek Dupnitsa v FK Kyustendil | L | 1-0 |
| Bulgaria Third League | 2022/12/03 12:00 | Granit Vladaya v FK Kyustendil | W | 0-6 |