Home History
| North Macedonia Second League | 2023/10/21 12:00 | FK Kozuf Gevgelija v Pobeda Valandovo | D | 0-0 |
| North Macedonia Second League | 2023/10/08 12:00 | Pobeda Valandovo v Detonit Plackovica | W | 2-0 |
| North Macedonia Second League | 2023/09/30 12:00 | FK Sasa v Pobeda Valandovo | L | 2-1 |
| North Macedonia Second League | 2023/09/23 13:00 | Pobeda Valandovo v Novaci | D | 1-1 |
| North Macedonia Second League | 2023/09/16 13:00 | Belasica Strumica v Pobeda Valandovo | L | 3-1 |
| North Macedonia Second League | 2023/09/03 14:00 | Pobeda Valandovo v Osogovo Kocani | W | 1-0 |
| North Macedonia Second League | 2023/08/26 14:00 | Pobeda Valandovo v Ohrid | D | 0-0 |
| North Macedonia Second League | 2023/08/19 15:00 | KF Bashkimi v Pobeda Valandovo | L | 2-1 |
Away History
| 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 |
| North Macedonia Second League | 2023/09/30 12:00 | FK Karaorman v KF Besa Doberdoll | L | 0-2 |
| North Macedonia Second League | 2023/09/23 13:00 | Pelister Bitola v FK Karaorman | L | 4-1 |
| North Macedonia Second League | 2023/09/16 13:00 | FK Karaorman v KF Arsimi | L | 0-6 |
| North Macedonia Second League | 2023/09/03 14:00 | FK Skopje v FK Karaorman | L | 2-1 |
| North Macedonia Second League | 2023/08/30 14:00 | Ohrid v FK Karaorman | L | 1-0 |
| North Macedonia Second League | 2023/08/26 14:00 | FK Karaorman v FK Vardar Negotino | W | 2-0 |