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| Date | Match | Score |
|---|---|---|
| 13.09.2025 | Osogovo - Skopje | 2 : 3 |
| 22.02.2025 | Skopje - Osogovo | 0 : 0 |
| 24.08.2024 | Osogovo - Skopje | 1 : 1 |
| 04.05.2024 | Osogovo - Skopje | 2 : 1 |
| 27.11.2023 | Skopje - Osogovo | 1 : 0 |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.09.2026 | Kozuv Gevgelija - Skopje | 0 - 1 | W |
| 05.09.2026 | Skopje - Bashkimi Kumanovo | 1 - 2 | L |
| 29.08.2026 | Aresimi - Skopje | 0 - 0 | D |
| 21.08.2026 | Skopje - Tikveš | 1 - 1 | D |
| 15.08.2026 | Sileks - Skopje | 3 - 0 | L |
| 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 |