[2] KF Shkupi Skopje 2-2 Shkendija Tetovo [2] 2020-08-09 15:30
Stadium: Cair Stadium Round: 1
Home Manager: Muharem Bajrami Away Manager: Erhan Selimi
Head to Head
| North Macedonia First League | 2019/12/01 12:00 | Shkendija Tetovo v KF Shkupi Skopje | L | 4-0 |
| North Macedonia First League | 2019/09/28 13:00 | KF Shkupi Skopje v Shkendija Tetovo | W | 2-0 |
| North Macedonia First League | 2019/04/27 14:00 | Shkendija Tetovo v KF Shkupi Skopje | L | 5-1 |
| North Macedonia First League | 2019/03/10 13:00 | KF Shkupi Skopje v Shkendija Tetovo | W | 1-0 |
| North Macedonia First League | 2018/11/04 12:30 | Shkendija Tetovo v KF Shkupi Skopje | L | 3-0 |
| North Macedonia First League | 2018/09/02 14:15 | KF Shkupi Skopje v Shkendija Tetovo | L | 1-2 |
| North Macedonia First League | 2018/04/22 14:00 | Shkendija Tetovo v KF Shkupi Skopje | L | 2-0 |
| North Macedonia First League | 2018/02/18 13:00 | KF Shkupi Skopje v Shkendija Tetovo | L | 0-3 |
Home History
| 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 |
| Europe Friendlies | 2020/07/18 15:30 | Ohrid v KF Shkupi Skopje | W | 1-3 |
| 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 | Akademija Pandev 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 |
Away History
| Europe Friendlies | 2020/08/01 17:30 | Bregalnica Stip v Shkendija Tetovo | W | 0-2 |
| Europe Friendlies | 2020/07/24 15:00 | Shkendija Tetovo v Rabotnicki Skopje | W | 2-0 |
| Europe Friendlies | 2020/07/19 15:00 | Shkendija Tetovo v Makedonija Gj. P | D | 1-1 |
| Europe Friendlies | 2020/07/16 15:00 | FK Gostivar v Shkendija Tetovo | W | 0-1 |
| North Macedonia First League | 2020/03/11 13:00 | Shkendija Tetovo v Rabotnicki Skopje | L | 0-1 |
| North Macedonia First League | 2020/03/08 13:00 | FK Borec v Shkendija Tetovo | L | 4-2 |
| North Macedonia Cup | 2020/03/04 13:00 | Rabotnicki Skopje v Shkendija Tetovo | D | 2-2 |
| North Macedonia First League | 2020/03/01 13:00 | Shkendija Tetovo v Makedonija Gj. P | W | 4-1 |