[10] Vardar Skopje 1-0 KF Shkupi Skopje [3] 2020-09-13 14:00
Stadium: Tose Proeski National Arena Round: 5
Home Manager: Aleksandar Vasoski Away Manager: Muharem Bajrami
Head to Head
| North Macedonia First League | 2019/11/24 12:00 | Vardar Skopje v KF Shkupi Skopje | D | 1-1 |
| North Macedonia First League | 2019/09/18 13:30 | KF Shkupi Skopje v Vardar Skopje | W | 1-2 |
| North Macedonia First League | 2019/05/04 14:00 | KF Shkupi Skopje v Vardar Skopje | D | 2-2 |
| North Macedonia First League | 2019/03/16 13:30 | Vardar Skopje v KF Shkupi Skopje | W | 1-0 |
| North Macedonia First League | 2018/11/10 12:00 | KF Shkupi Skopje v Vardar Skopje | L | 1-0 |
| North Macedonia First League | 2018/09/16 13:30 | Vardar Skopje v KF Shkupi Skopje | W | 2-1 |
| North Macedonia First League | 2018/05/20 14:15 | KF Shkupi Skopje v Vardar Skopje | L | 4-1 |
| North Macedonia First League | 2018/04/15 14:00 | Vardar Skopje v KF Shkupi Skopje | D | 1-1 |
Home History
| Europe Friendlies | 2020/09/06 17:00 | FK Lokomotive v Vardar Skopje | W | 1-4 |
| North Macedonia First League | 2020/08/29 14:30 | Rabotnicki Skopje v Vardar Skopje | D | 1-1 |
| North Macedonia First League | 2020/08/23 15:00 | Vardar Skopje v FK Sileks | L | 0-4 |
| North Macedonia First League | 2020/08/16 15:00 | Akademija Pandev v Vardar Skopje | W | 0-1 |
| North Macedonia First League | 2020/08/08 15:30 | Vardar Skopje v FK Borec | L | 0-1 |
| North Macedonia First League | 2020/03/11 13:00 | Vardar Skopje v FC Struga Trim & Lum | W | 1-0 |
| North Macedonia First League | 2020/03/08 12:00 | Renova Dzepciste v Vardar Skopje | L | 2-0 |
| North Macedonia First League | 2020/02/29 13:00 | Vardar Skopje v Rabotnicki Skopje | D | 0-0 |
Away History
| Europe Friendlies | 2020/09/06 14:30 | KF Shkupi Skopje v Osogovo Kocani | W | 4-0 |
| 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 |