Transfers snapshot
- Osogovo has 15 recorded transfers. (6 in, 9 out).
| Player | Direction | Date | Type | From | To |
|---|---|---|---|---|---|
 Hristijan Pop-Antoski | Out | 2026-08-14 | - | Osogovo |  FK Rabotnicki RAB |
 Hristijan Mitrevski | Out | 2026-08-14 | Transfer | Osogovo | FK Rabotnicki RAB |
 Stojche Stojov | In | 2026-06-29 | - |  Sileks SIL | Osogovo |
 D. Golubov | Out | 2026-02-09 | Free agent | Osogovo |  Tikveš |
 S. Velinov | In | 2026-01-09 | Free agent |  Nesebar | Osogovo |
 V. Zhoglev | Out | 2025-12-08 | - | Osogovo |  Shkëndija Haraçinë |
| Stojche Stojov | Out | 2025-06-30 | Transfer | Osogovo | Sileks SIL |
 Darko Jocikj | Out | 2020-01-01 | N/A | Osogovo |  Borec BOR |
| Darko Jocikj | In | 2019-08-01 | Loan | Borec BOR | Osogovo |
 S. Mitevski | Out | 2019-07-01 | Free | Osogovo | Sileks SIL |
 V. Zhoglev | Out | 2018-06-16 | Free | Osogovo |  Pobeda POB |
| S. Mitevski | In | 2018-02-01 | N/A | Sileks SIL | Osogovo |
 Vlatko Kocev | Out | 2018-02-01 | Free | Osogovo |  Skopje SKO |
 Darko Lazarevski | In | 2011-01-01 | Free |  Vardar Skopje VAR | Osogovo |
| Vlatko Kocev | In | 2010-07-01 | N/A |  Bregalnica Štip BRE | Osogovo |