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| Date | Match | Score |
|---|---|---|
| 15.11.2025 | Kyustendil - Septemvri Simitli | 1 : 0 |
| 04.06.2025 | Septemvri Simitli - Kyustendil | 3 : 1 |
| 23.11.2024 | Kyustendil - Septemvri Simitli | 3 : 0 |
| 16.03.2024 | Kyustendil - Septemvri Simitli | 3 : 3 |
| 02.09.2023 | Septemvri Simitli - Kyustendil | 2 : 2 |
| 19.11.2022 | Septemvri Simitli - Kyustendil | 1 : 1 |
| 03.09.2022 | Kyustendil - Septemvri Simitli | 2 : 1 |
| 23.11.2019 | Septemvri Simitli - Kyustendil | 2 : 0 |
| Date | Match | Score | Res |
|---|---|---|---|
| 05.09.2026 | Pirin Razlog - Septemvri Simitli | 1 - 1 | D |
| 29.08.2026 | Septemvri Simitli - Natsional Sofia | 3 - 3 | D |
| 22.08.2026 | Chavdar Etropole - Septemvri Simitli | 4 - 2 | L |
| 15.08.2026 | Septemvri Simitli - CSKA Sofia III | 0 - 0 | D |
| 08.08.2026 | Balkan Botevgrad - Septemvri Simitli | 1 - 2 | W |
| Date | Match | Score | Res |
|---|---|---|---|
| 05.09.2026 | Natsional Sofia - Kyustendil | 1 - 1 | D |
| 29.08.2026 | Kyustendil - Chavdar Etropole | 3 - 1 | W |
| 22.08.2026 | CSKA Sofia III - Kyustendil | 1 - 1 | D |
| 15.08.2026 | Kyustendil - Balkan Botevgrad | 0 - 1 | L |
| 08.08.2026 | Kostinbrod - Kyustendil | 3 - 1 | L |