[9] KF Shkupi Skopje 1-1 FK Sileks [3] 2023-08-20 15:00
Stadium: Cair Stadium Round: 3
Home Manager: Cihat Arslan Away Manager: Gorazd Mihajlov
Head to Head
| North Macedonia First League | 2023/04/30 14:00 | FK Sileks v KF Shkupi Skopje | W | 0-2 |
| North Macedonia First League | 2023/02/26 13:00 | FK Sileks v KF Shkupi Skopje | L | 2-1 |
| North Macedonia First League | 2022/10/02 13:00 | KF Shkupi Skopje v FK Sileks | D | 0-0 |
| North Macedonia First League | 2021/03/20 14:00 | FK Sileks v KF Shkupi Skopje | W | 1-3 |
| North Macedonia First League | 2021/03/03 13:00 | FK Sileks v KF Shkupi Skopje | W | 0-1 |
| North Macedonia First League | 2020/10/24 12:30 | KF Shkupi Skopje v FK Sileks | W | 1-0 |
| North Macedonia First League | 2020/03/11 13:00 | KF Shkupi Skopje v FK Sileks | D | 1-1 |
| North Macedonia First League | 2019/11/09 12:00 | FK Sileks v KF Shkupi Skopje | L | 1-0 |
Home History
| North Macedonia First League | 2023/08/13 15:00 | Vardar Skopje v KF Shkupi Skopje | W | 0-1 |
| North Macedonia First League | 2023/08/07 15:00 | Rabotnicki Skopje v KF Shkupi Skopje | L | 3-1 |
| UEFA Conference League Qualifying | 2023/08/03 17:00 | Levski Sofia v KF Shkupi Skopje | L | 1-0 |
| UEFA Conference League Qualifying | 2023/07/27 19:00 | KF Shkupi Skopje v Levski Sofia | L | 0-2 |
| UEFA Conference League Qualifying | 2023/07/20 19:00 | KF Shkupi Skopje v Hegelmann Litauen | D | 0-0 |
| UEFA Conference League Qualifying | 2023/07/13 17:00 | Hegelmann Litauen v KF Shkupi Skopje | W | 0-5 |
| North Macedonia First League | 2023/05/14 15:00 | FC Struga Trim & Lum v KF Shkupi Skopje | L | 2-1 |
| North Macedonia First League | 2023/05/10 15:00 | KF Shkupi Skopje v Makedonija Gj. P | W | 3-0 |
Away History
| North Macedonia First League | 2023/08/13 15:00 | FK Sileks v Rabotnicki Skopje | W | 2-0 |
| North Macedonia First League | 2023/08/06 15:00 | Bregalnica Stip v FK Sileks | L | 2-1 |
| North Macedonia First League | 2023/05/14 15:00 | Akademija Pandev v FK Sileks | D | 2-2 |
| North Macedonia First League | 2023/05/10 15:00 | FK Sileks v Rabotnicki Skopje | W | 2-0 |
| North Macedonia First League | 2023/05/07 15:00 | FC Struga Trim & Lum v FK Sileks | L | 3-0 |
| North Macedonia First League | 2023/04/30 14:00 | FK Sileks v KF Shkupi Skopje | L | 0-2 |
| North Macedonia First League | 2023/04/26 14:00 | Shkendija Tetovo v FK Sileks | D | 0-0 |
| North Macedonia First League | 2023/04/23 14:00 | FK Sileks v Makedonija Gj. P | W | 1-0 |