Head to Head
| Club Friendly List | 2020/02/14 12:00 | FK Kyustendil v Septemvri Simitli | L | 2-0 |
Home History
| Europe Friendlies | 2021/01/27 12:00 | Lokomotiv 1929 Sofia v Septemvri Simitli | D | 0-0 |
| Club Friendly List | 2021/01/20 08:00 | FK Khimki v Septemvri Simitli | D | 1-1 |
| Bulgaria B PFG | 2020/12/12 12:00 | PFC Dobrudzha Dobrich v Septemvri Simitli | W | 0-2 |
| Bulgaria B PFG | 2020/12/04 12:00 | Septemvri Simitli v Minyor Pernik | W | 3-0 |
| Bulgaria B PFG | 2020/11/27 12:45 | Lokomotiv 1929 Sofia v Septemvri Simitli | L | 2-0 |
| Bulgaria B PFG | 2020/11/20 12:00 | Septemvri Simitli v Neftochimik 1962 | L | 1-2 |
| Europe Friendlies | 2020/11/14 11:00 | Botev Plovdiv v Septemvri Simitli | L | 3-2 |
| Bulgaria B PFG | 2020/11/07 12:30 | Lokomotiv Gorna Oryahovitsa v Septemvri Simitli | L | 3-0 |
Away History
| Bulgaria Third League | 2020/11/14 12:00 | Chavdar Etropole v FK Kyustendil | L | 1-0 |
| Bulgaria Third League | 2020/10/17 13:00 | Nadezhda Dobroslavci v FK Kyustendil | W | 0-2 |
| Bulgaria Amateur Cup | 2020/09/23 14:00 | Marek Dupnitsa v FK Kyustendil | L | 3-0 |
| Bulgaria Third League | 2020/09/19 14:00 | Pirin 2002 v FK Kyustendil | W | 0-3 |
| Bulgaria Third League | 2020/09/05 14:00 | Belasitsa v FK Kyustendil | L | 1-0 |
| Club Friendly List | 2020/02/14 12:00 | FK Kyustendil v Septemvri Simitli | W | 2-0 |
| Europe Friendlies | 2020/01/25 12:00 | FK Kyustendil v Marek Dupnitsa | L | 2-3 |
| Bulgaria Third League | 2019/11/06 12:00 | Minyor Pernik v FK Kyustendil | L | 4-0 |