[6] KF Shkupi Skopje 3-1 Akademija Pandev [2] 2019-11-27 12:00
Stadium: Cair Stadium Round: 16
Home Manager: Recai Sahinler Away Manager: Jugoslav Trencovski
Head to Head
| North Macedonia First League | 2019/09/22 13:30 | Akademija Pandev v KF Shkupi Skopje | D | 0-0 |
| North Macedonia First League | 2019/04/24 14:00 | KF Shkupi Skopje v Akademija Pandev | W | 1-0 |
| North Macedonia First League | 2019/03/03 13:00 | Akademija Pandev v KF Shkupi Skopje | W | 0-2 |
| North Macedonia First League | 2018/10/31 12:30 | KF Shkupi Skopje v Akademija Pandev | W | 1-0 |
| North Macedonia First League | 2018/08/26 14:30 | Akademija Pandev v KF Shkupi Skopje | L | 1-0 |
| North Macedonia First League | 2018/04/18 14:00 | Akademija Pandev v KF Shkupi Skopje | W | 1-2 |
| North Macedonia First League | 2018/02/14 13:00 | KF Shkupi Skopje v Akademija Pandev | W | 5-2 |
| North Macedonia First League | 2017/10/14 12:30 | Akademija Pandev v KF Shkupi Skopje | L | 2-0 |
Home History
| North Macedonia First League | 2019/11/24 12:00 | Vardar Skopje v KF Shkupi Skopje | D | 1-1 |
| North Macedonia First League | 2019/11/09 12:00 | FK Sileks v KF Shkupi Skopje | L | 1-0 |
| North Macedonia First League | 2019/11/03 12:30 | KF Shkupi Skopje v FC Struga Trim & Lum | D | 0-0 |
| North Macedonia Cup | 2019/10/30 12:30 | FK Sileks v KF Shkupi Skopje | D | 1-1 |
| North Macedonia First League | 2019/10/27 12:30 | Renova Dzepciste v KF Shkupi Skopje | D | 2-2 |
| North Macedonia First League | 2019/10/23 12:30 | KF Shkupi Skopje v Rabotnicki Skopje | W | 2-0 |
| North Macedonia First League | 2019/10/19 12:30 | FK Borec v KF Shkupi Skopje | L | 2-1 |
| North Macedonia First League | 2019/10/05 13:00 | Makedonija Gj. P v KF Shkupi Skopje | D | 0-0 |
Away History
| North Macedonia First League | 2019/11/24 12:00 | Akademija Pandev v FC Struga Trim & Lum | D | 1-1 |
| North Macedonia First League | 2019/11/09 12:00 | Renova Dzepciste v Akademija Pandev | D | 1-1 |
| North Macedonia First League | 2019/11/02 12:30 | Akademija Pandev v Rabotnicki Skopje | D | 1-1 |
| North Macedonia Cup | 2019/10/30 12:30 | Osogovo Kocani v Akademija Pandev | W | 1-4 |
| North Macedonia First League | 2019/10/27 12:30 | FK Borec v Akademija Pandev | L | 1-0 |
| North Macedonia First League | 2019/10/23 12:30 | Akademija Pandev v Makedonija Gj. P | W | 4-0 |
| North Macedonia First League | 2019/10/18 12:30 | Shkendija Tetovo v Akademija Pandev | W | 0-1 |
| North Macedonia First League | 2019/10/05 13:00 | Akademija Pandev v FK Sileks | W | 2-0 |