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| Date | Match | Score |
|---|---|---|
| 23.04.2022 | Osogovo - Sloga Vinica | 0 : 1 |
| 20.11.2021 | Osogovo - Sloga Vinica | 3 : 0 |
| 29.08.2021 | Sloga Vinica - Osogovo | 1 : 0 |
| 01.05.2021 | Sloga Vinica - Osogovo | 4 : 1 |
| 28.11.2020 | Sloga Vinica - Osogovo | 3 : 0 |
| 26.09.2020 | Osogovo - Sloga Vinica | 1 : 1 |
| 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 |
|---|---|---|---|
| 23.05.2026 | Ohrid - Sloga Vinica | 7 - 1 | L |
| 16.05.2026 | Sloga Vinica - FK Prespa Resen | 3 - 2 | W |
| 10.05.2026 | Sasa - Sloga Vinica | 1 - 0 | L |
| 02.05.2026 | Sloga Vinica - Novaci | 0 - 0 | D |
| 25.04.2026 | Bregalnica Štip - Sloga Vinica | 4 - 1 | L |