Home History
| 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 |
| Europe Friendlies | 2019/07/24 15:00 | FK Kyustendil v Minyor Pernik | W | 3-1 |
Away History
| Europe Friendlies | 2020/01/21 23:00 | Botev Ihtiman v Septemvri Simitli | W | 2-3 |
| Bulgaria Third League | 2019/11/06 12:00 | Botev Ihtiman v Septemvri Simitli | W | 0-1 |
| Bulgaria Third League | 2019/08/19 15:00 | Balkan Botevgrad v Septemvri Simitli | D | 2-2 |
| Bulgaria Third League | 2019/08/10 17:00 | Septemvri Simitli v Belasitsa | W | 3-1 |
| Europe Friendlies | 2019/07/24 15:00 | Septemvri Simitli v Botev Ihtiman | W | 2-0 |
| Europe Friendlies | 2019/07/12 07:00 | FC Hebar Pazardzhik v Septemvri Simitli | L | 1-0 |
| Europe Friendlies | 2019/07/10 15:00 | Rilski Sportist v Septemvri Simitli | W | 2-3 |
| Europe Friendlies | 2019/07/03 08:00 | Belasitsa v Septemvri Simitli | L | 2-0 |