Head to Head
| North Macedonia Second League | 2023/11/04 12:00 | FK Karaorman v Osogovo Kocani | L | 2-0 |
Home History
| North Macedonia Second League | 2024/04/20 14:00 | FK Kozuf Gevgelija v Osogovo Kocani | L | 2-0 |
| North Macedonia Second League | 2024/04/13 13:00 | Osogovo Kocani v Detonit Plackovica | L | 1-3 |
| North Macedonia Second League | 2024/04/06 13:00 | FK Sasa v Osogovo Kocani | L | 2-1 |
| North Macedonia Second League | 2024/03/30 14:00 | Osogovo Kocani v Novaci | W | 1-0 |
| North Macedonia Second League | 2024/03/17 14:00 | Belasica Strumica v Osogovo Kocani | D | 1-1 |
| North Macedonia Second League | 2024/03/09 13:00 | Ohrid v Osogovo Kocani | L | 5-0 |
| North Macedonia Second League | 2024/03/05 13:00 | Osogovo Kocani v Pobeda Valandovo | D | 0-0 |
| North Macedonia Second League | 2024/03/02 13:00 | KF Bashkimi v Osogovo Kocani | L | 2-1 |
Away History
| North Macedonia Second League | 2024/04/20 14:00 | FK Karaorman v Pobeda Valandovo | L | 0-2 |
| North Macedonia Second League | 2024/04/13 13:00 | KF Bashkimi v FK Karaorman | L | 5-1 |
| North Macedonia Second League | 2024/04/06 13:00 | FK Karaorman v Teteks Tetovo | L | 1-4 |
| North Macedonia Second League | 2024/03/30 14:00 | KF Besa Doberdoll v FK Karaorman | L | 3-0 |
| North Macedonia Second League | 2024/03/17 14:00 | FK Karaorman v Pelister Bitola | L | 1-4 |
| North Macedonia Second League | 2024/03/09 13:00 | KF Arsimi v FK Karaorman | L | 3-0 |
| North Macedonia Second League | 2024/03/05 13:00 | FK Karaorman v FK Skopje | L | 0-1 |
| North Macedonia Second League | 2024/03/02 13:00 | FK Vardar Negotino v FK Karaorman | L | 2-0 |