Home History
| North Macedonia First League | 2020/08/30 14:30 | KF Shkupi Skopje v Pelister Bitola | W | 1-0 |
| UEFA Europa League Qualifying | 2020/08/27 16:00 | Neftchi Baku v KF Shkupi Skopje | L | 2-1 |
| North Macedonia First League | 2020/08/21 15:00 | Belasica Strumica v KF Shkupi Skopje | W | 0-2 |
| North Macedonia First League | 2020/08/16 15:00 | KF Shkupi Skopje v Makedonija Gj. P | W | 3-1 |
| North Macedonia First League | 2020/08/09 15:30 | KF Shkupi Skopje v Shkendija Tetovo | D | 2-2 |
| Europe Friendlies | 2020/07/30 15:30 | FK Vardari Forino v KF Shkupi Skopje | W | 1-2 |
| Europe Friendlies | 2020/07/26 15:00 | FC Struga Trim & Lum v KF Shkupi Skopje | L | 2-1 |
| Europe Friendlies | 2020/07/22 15:30 | Renova Dzepciste v KF Shkupi Skopje | L | 1-0 |
Away History
| North Macedonia Second League | 2020/08/30 14:30 | FK Lokomotive v Osogovo Kocani | D | 3-3 |
| North Macedonia Second League | 2020/08/22 15:00 | FK Kozuf Gevgelija v Osogovo Kocani | L | 2-0 |
| North Macedonia Second League | 2020/03/07 13:00 | FK Kozuf Gevgelija v Osogovo Kocani | L | 1-0 |
| North Macedonia Second League | 2020/02/29 13:00 | Osogovo Kocani v Belasica Strumica | L | 0-2 |
| Europe Friendlies | 2020/02/12 13:30 | FK Kozuf Gevgelija v Osogovo Kocani | L | 3-1 |
| Europe Friendlies | 2020/02/02 12:00 | FK Sasa v Osogovo Kocani | D | 2-2 |
| North Macedonia Second League | 2019/11/30 12:00 | Pobeda Valandovo v Osogovo Kocani | L | 5-1 |
| North Macedonia Second League | 2019/11/23 12:00 | Osogovo Kocani v FK Lokomotive | L | 1-2 |