Head to Head
| Bulgaria Third League | 2025/06/04 16:00 | Septemvri Simitli v FK Kyustendil | L | 3-1 |
| Bulgaria Third League | 2024/11/23 12:00 | FK Kyustendil v Septemvri Simitli | W | 3-0 |
| Bulgaria Third League | 2023/09/02 14:00 | Septemvri Simitli v FK Kyustendil | D | 2-2 |
| 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 | W | 1-2 |
| Club Friendly List | 2020/02/14 12:00 | FK Kyustendil v Septemvri Simitli | W | 2-0 |
Home History
| Bulgaria Third League | 2025/06/04 16:00 | Septemvri Simitli v FK Kyustendil | L | 3-1 |
| Bulgaria Third League | 2025/05/31 15:00 | FK Kyustendil v PFC CSKA Sofia III | W | 5-1 |
| Bulgaria Third League | 2025/05/14 15:00 | Slivnishki Geroy v FK Kyustendil | D | 2-2 |
| Bulgaria Third League | 2025/04/26 14:00 | FK Kyustendil v Pirin Gotse Delchev | W | 4-1 |
| Bulgaria Third League | 2025/04/23 14:00 | Oborishte v FK Kyustendil | L | 2-1 |
| Bulgaria Third League | 2025/02/22 12:00 | FK Kyustendil v PFC Pirin Blagoevgrad II | W | 5-0 |
| Bulgaria Third League | 2024/11/23 12:00 | FK Kyustendil v Septemvri Simitli | W | 3-0 |
| Bulgaria Third League | 2024/11/16 12:00 | PFC CSKA Sofia III v FK Kyustendil | W | 2-4 |
Away History
| Bulgaria Third League | 2025/06/04 16:00 | Septemvri Simitli v FK Kyustendil | W | 3-1 |
| Bulgaria Third League | 2025/05/31 13:00 | Botev Ihtiman v Septemvri Simitli | D | 2-2 |
| Bulgaria Third League | 2025/05/17 12:00 | CSKA 1948 III v Septemvri Simitli | L | 2-1 |
| Bulgaria Third League | 2025/05/10 15:00 | FK Vitosha Bistrica v Septemvri Simitli | L | 2-1 |
| Bulgaria Third League | 2025/05/06 12:00 | Septemvri Simitli v PFC Levski Sofia II | W | 1-0 |
| Bulgaria Third League | 2025/05/03 15:00 | Septemvri Simitli v Balkan Botevgrad | W | 4-3 |
| Bulgaria Third League | 2025/04/30 14:00 | Septemvri Sofia II v Septemvri Simitli | W | 0-2 |
| Bulgaria Third League | 2025/04/13 14:00 | PFC Pirin Blagoevgrad II v Septemvri Simitli | L | 2-0 |
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