Head to Head
| 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 Second League | 2022/05/21 13:45 | Septemvri Simitli v FC Hebar Pazardzhik | L | 1-2 |
| Bulgaria Second League | 2022/05/15 15:00 | Ludogorets Razgrad II v Septemvri Simitli | L | 4-0 |
| Bulgaria Second League | 2022/05/07 15:00 | Septemvri Simitli v Levski Lom | W | 3-0 |
| Bulgaria Second League | 2022/05/04 15:00 | PFC Dobrudzha Dobrich v Septemvri Simitli | L | 3-0 |
| Bulgaria Second League | 2022/04/30 14:00 | Septemvri Simitli v FC Lovech | L | 1-2 |
| Bulgaria Second League | 2022/04/21 14:00 | Maritsa Plovdiv v Septemvri Simitli | W | 1-2 |
| Bulgaria Second League | 2022/04/16 14:00 | Septemvri Simitli v CSKA 1948 Sofia II | L | 1-4 |
| Bulgaria Second League | 2022/04/10 14:00 | Spartak Varna v Septemvri Simitli | L | 3-1 |
Away History
| Bulgaria Third League | 2022/11/13 12:00 | FK Kyustendil v CSKA Sofia II | W | 2-1 |
| Bulgaria Third League | 2022/10/29 13:00 | FK Kyustendil v Pirin 2002 | W | 3-0 |
| Bulgaria Third League | 2022/10/08 13:00 | FK Kyustendil v Nadezhda Dobroslavci | W | 4-0 |
| Bulgaria Amateur Cup | 2022/09/07 14:00 | Marek Dupnitsa v FK Kyustendil | L | 3-1 |
| Bulgaria Third League | 2022/08/21 15:00 | FK Kyustendil v PFC Levski Sofia II | W | 4-0 |
| Bulgaria Third League | 2022/06/04 15:00 | Balkan Botevgrad v FK Kyustendil | W | 1-2 |
| Bulgaria Third League | 2022/05/21 15:00 | Granit Vladaya v FK Kyustendil | W | 0-1 |
| Bulgaria Third League | 2022/05/18 15:00 | FK Kyustendil v Chavdar Etropole | L | 0-1 |