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 | 2023/12/09 12:00 | Pelister Bitola v Osogovo Kocani | L | 2-1 |
| North Macedonia Second League | 2023/12/02 12:00 | Osogovo Kocani v KF Arsimi | D | 1-1 |
| North Macedonia Second League | 2023/11/27 12:00 | FK Skopje v Osogovo Kocani | L | 1-0 |
| North Macedonia Second League | 2023/11/12 12:00 | Osogovo Kocani v FK Vardar Negotino | D | 2-2 |
| North Macedonia Second League | 2023/11/04 12:00 | FK Karaorman v Osogovo Kocani | L | 2-0 |
| North Macedonia Second League | 2023/10/28 11:00 | Osogovo Kocani v FK Kozuf Gevgelija | W | 3-2 |
| North Macedonia Second League | 2023/10/21 12:00 | Detonit Plackovica v Osogovo Kocani | L | 3-0 |
| North Macedonia Second League | 2023/10/07 12:00 | Osogovo Kocani v FK Sasa | D | 1-1 |
Away History
| North Macedonia Second League | 2023/12/09 12:00 | FK Karaorman v Detonit Plackovica | L | 0-1 |
| North Macedonia Second League | 2023/12/02 12:00 | FK Sasa v FK Karaorman | D | 2-2 |
| North Macedonia Second League | 2023/11/25 12:00 | FK Karaorman v Novaci | L | 1-3 |
| North Macedonia Second League | 2023/11/12 12:00 | Belasica Strumica v FK Karaorman | L | 2-1 |
| North Macedonia Second League | 2023/11/04 12:00 | FK Karaorman v Osogovo Kocani | W | 2-0 |
| North Macedonia Second League | 2023/10/28 11:00 | Pobeda Valandovo v FK Karaorman | W | 1-2 |
| North Macedonia Second League | 2023/10/21 12:00 | FK Karaorman v KF Bashkimi | L | 1-2 |
| North Macedonia Second League | 2023/10/08 12:00 | Teteks Tetovo v FK Karaorman | D | 1-1 |