[2] KF Shkupi Skopje 1-1 Vardar Skopje [7] 2020-12-09 12:00
Stadium: Cair Stadium Round: 16
Home Manager: Umit Karan Away Manager: Aleksandar Vasoski
Head to Head
| North Macedonia First League | 2020/09/13 14:00 | Vardar Skopje v KF Shkupi Skopje | L | 1-0 |
| 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 | L | 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 | L | 1-0 |
| North Macedonia First League | 2018/11/10 12:00 | KF Shkupi Skopje v Vardar Skopje | W | 1-0 |
| North Macedonia First League | 2018/09/16 13:30 | Vardar Skopje v KF Shkupi Skopje | L | 2-1 |
| North Macedonia First League | 2018/05/20 14:15 | KF Shkupi Skopje v Vardar Skopje | W | 4-1 |
Home History
| North Macedonia First League | 2020/12/06 12:00 | Pelister Bitola v KF Shkupi Skopje | W | 1-3 |
| North Macedonia First League | 2020/12/02 12:00 | KF Shkupi Skopje v Belasica Strumica | W | 3-1 |
| North Macedonia First League | 2020/11/29 12:00 | Makedonija Gj. P v KF Shkupi Skopje | D | 0-0 |
| North Macedonia Cup | 2020/11/25 12:00 | Akademija Pandev v KF Shkupi Skopje | L | 2-1 |
| North Macedonia First League | 2020/11/22 12:00 | Shkendija Tetovo v KF Shkupi Skopje | D | 1-1 |
| North Macedonia First League | 2020/11/07 12:30 | Rabotnicki Skopje v KF Shkupi Skopje | D | 2-2 |
| North Macedonia First League | 2020/10/24 12:30 | KF Shkupi Skopje v FK Sileks | W | 1-0 |
| North Macedonia Cup | 2020/10/21 12:30 | KF Shkupi Skopje v FK Lokomotive | W | 5-0 |
Away History
| North Macedonia First League | 2020/12/06 12:00 | Vardar Skopje v Rabotnicki Skopje | D | 0-0 |
| North Macedonia First League | 2020/12/02 12:00 | FK Sileks v Vardar Skopje | L | 1-0 |
| North Macedonia First League | 2020/11/28 12:00 | Vardar Skopje v Akademija Pandev | W | 2-0 |
| North Macedonia First League | 2020/11/21 12:00 | FK Borec v Vardar Skopje | W | 0-2 |
| North Macedonia First League | 2020/11/07 12:30 | FC Struga Trim & Lum v Vardar Skopje | D | 2-2 |
| North Macedonia First League | 2020/10/25 13:30 | Vardar Skopje v Renova Dzepciste | D | 3-3 |
| North Macedonia Cup | 2020/10/21 12:30 | Akademija Pandev v Vardar Skopje | L | 1-0 |
| North Macedonia First League | 2020/10/17 12:30 | Vardar Skopje v Shkendija Tetovo | L | 1-5 |