Home History
| North Macedonia First League | 2020/03/11 13:00 | KF Shkupi Skopje v FK Sileks | D | 1-1 |
| North Macedonia First League | 2020/03/08 13:00 | FC Struga Trim & Lum v KF Shkupi Skopje | W | 1-2 |
| North Macedonia Cup | 2020/03/04 13:00 | AP Brera Strumica v KF Shkupi Skopje | D | 1-1 |
| North Macedonia First League | 2020/03/01 13:00 | KF Shkupi Skopje v Renova Dzepciste | L | 2-3 |
| North Macedonia First League | 2020/02/23 13:00 | Rabotnicki Skopje v KF Shkupi Skopje | L | 2-1 |
| North Macedonia First League | 2020/02/16 13:00 | KF Shkupi Skopje v FK Borec | W | 2-0 |
| Europe Friendlies | 2020/01/19 12:30 | KF Shkupi Skopje v KF Drita | D | 0-0 |
| Club Friendly List | 2020/01/16 12:00 | KF Shkupi Skopje v Flamurtari | D | 0-0 |
Away History
| 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 |
| North Macedonia Second League | 2019/11/10 12:00 | Tikves Kavadarci v Osogovo Kocani | L | 7-1 |
| North Macedonia Second League | 2019/11/02 12:30 | Osogovo Kocani v Bregalnica Stip | L | 1-2 |