[5] FK Sileks 1-0 KF Shkupi Skopje [3] 2019-11-09 12:00
Stadium: Gradski Stadion Kratovo Round: 14
Home Manager: Goran Simov Away Manager: Recai Sahinler
Head to Head
| North Macedonia Cup | 2019/10/30 12:30 | FK Sileks v KF Shkupi Skopje | D | 1-1 |
| North Macedonia Cup | 2019/09/25 13:30 | KF Shkupi Skopje v FK Sileks | D | 0-0 |
| North Macedonia First League | 2019/09/14 13:30 | KF Shkupi Skopje v FK Sileks | L | 1-0 |
| North Macedonia First League | 2019/04/14 14:00 | KF Shkupi Skopje v FK Sileks | L | 2-1 |
| North Macedonia First League | 2019/02/17 13:00 | FK Sileks v KF Shkupi Skopje | D | 2-2 |
| North Macedonia First League | 2018/10/21 12:30 | KF Shkupi Skopje v FK Sileks | L | 2-0 |
| North Macedonia First League | 2018/08/12 15:00 | FK Sileks v KF Shkupi Skopje | D | 1-1 |
| North Macedonia First League | 2018/05/02 14:00 | KF Shkupi Skopje v FK Sileks | D | 1-1 |
Home History
| North Macedonia First League | 2019/11/03 12:30 | Makedonija Gj. P v FK Sileks | W | 0-1 |
| 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 | FK Sileks v FC Struga Trim & Lum | W | 1-0 |
| North Macedonia First League | 2019/10/23 12:30 | Shkendija Tetovo v FK Sileks | L | 3-0 |
| North Macedonia First League | 2019/10/19 12:30 | FK Sileks v Renova Dzepciste | W | 3-0 |
| North Macedonia First League | 2019/10/05 13:00 | Akademija Pandev v FK Sileks | L | 2-0 |
| North Macedonia First League | 2019/09/29 13:00 | FK Sileks v Rabotnicki Skopje | W | 1-0 |
| North Macedonia Cup | 2019/09/25 13:30 | KF Shkupi Skopje v FK Sileks | D | 0-0 |
Away History
| 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 |
| North Macedonia First League | 2019/09/28 13:00 | KF Shkupi Skopje v Shkendija Tetovo | W | 2-0 |
| North Macedonia Cup | 2019/09/25 13:30 | KF Shkupi Skopje v FK Sileks | D | 0-0 |