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| Date | Match | Score |
|---|---|---|
| 16.05.2026 | Osogovo - Bregalnica Štip | 0 : 3 |
| 25.11.2025 | Bregalnica Štip - Osogovo | 0 : 1 |
| 08.03.2025 | Osogovo - Bregalnica Štip | 1 : 2 |
| 22.09.2024 | Bregalnica Štip - Osogovo | 1 : 1 |
| 24.04.2021 | Osogovo - Bregalnica Štip | 0 : 2 |
| 25.11.2020 | Osogovo - Bregalnica Štip | 1 : 3 |
| 19.09.2020 | Bregalnica Štip - Osogovo | 1 : 1 |
| 02.11.2019 | Osogovo - Bregalnica Štip | 1 : 2 |
| 31.08.2019 | Bregalnica Štip - Osogovo | 5 : 0 |
| 14.04.2018 | Osogovo - Bregalnica Štip | 0 : 0 |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.09.2026 | Osogovo - Belasica | 1 - 3 | L |
| 05.09.2026 | Detonit Plachkovica - Osogovo | 2 - 1 | L |
| 29.08.2026 | Osogovo - Novaci | 0 - 0 | D |
| 22.08.2026 | Kamjani - Osogovo | 2 - 1 | L |
| 15.08.2026 | Belasica - Osogovo | 1 - 0 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 04.09.2026 | Bregalnica Štip - Shkëndija Haraçinë | 0 - 1 | L |
| 28.08.2026 | Struga - Bregalnica Štip | 4 - 0 | L |
| 21.08.2026 | Bregalnica Štip - Bashkimi Kumanovo | 3 - 0 | W |
| 16.08.2026 | Shkendija - Bregalnica Štip | 4 - 1 | L |
| 08.08.2026 | Bregalnica Štip - Aresimi | 4 - 0 | W |