- 25/10/2025 Shkëndija Haraçinë
1 - 0 Osogovo Second League
- 11/10/2025 Osogovo
3 - 1 Belasica Second League
- 04/10/2025 Sloga Vinica
0 - 1 Osogovo Second League
- 01/11/2025 Teteks
- Osogovo Second League
- 08/11/2025 Osogovo
- Pobeda Second League
- 15/11/2025 Kozuv Gevgelija
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