Rabotnicki Skopje 3-1 KF Shkupi Skopje 2023-08-07 15:00
Stadium: Tose Proeski National Arena Round: 1
Home Manager: Milan Ilievski Away Manager: Cihat Arslan
Head to Head
| North Macedonia First League | 2023/03/12 13:00 | KF Shkupi Skopje v Rabotnicki Skopje | L | 3-1 |
| North Macedonia First League | 2022/12/11 12:00 | Rabotnicki Skopje v KF Shkupi Skopje | L | 2-4 |
| North Macedonia First League | 2022/09/11 14:00 | KF Shkupi Skopje v Rabotnicki Skopje | L | 5-0 |
| North Macedonia First League | 2022/03/12 14:00 | KF Shkupi Skopje v Rabotnicki Skopje | L | 2-0 |
| North Macedonia First League | 2022/02/20 13:00 | Rabotnicki Skopje v KF Shkupi Skopje | L | 0-1 |
| North Macedonia First League | 2021/10/03 13:00 | KF Shkupi Skopje v Rabotnicki Skopje | L | 2-0 |
| North Macedonia First League | 2021/04/25 11:00 | KF Shkupi Skopje v Rabotnicki Skopje | L | 2-0 |
| North Macedonia First League | 2021/03/07 13:00 | KF Shkupi Skopje v Rabotnicki Skopje | W | 0-2 |
Home History
| World Club Friendlies | 2023/07/27 15:30 | Rabotnicki Skopje v Al Ittifaq Dammam | L | 0-4 |
| Europe Friendlies | 2023/07/25 15:30 | Rabotnicki Skopje v Trabzonspor | L | 1-4 |
| Europe Friendlies | 2023/07/19 16:00 | Rabotnicki Skopje v MS Ashdod | L | 2-4 |
| North Macedonia First League | 2023/05/14 15:00 | Rabotnicki Skopje v Shkendija Tetovo | L | 1-2 |
| North Macedonia First League | 2023/05/10 15:00 | FK Sileks v Rabotnicki Skopje | L | 2-0 |
| North Macedonia First League | 2023/05/07 15:00 | Rabotnicki Skopje v Bregalnica Stip | W | 5-4 |
| North Macedonia First League | 2023/04/30 14:00 | Tikves Kavadarci v Rabotnicki Skopje | W | 1-3 |
| North Macedonia First League | 2023/04/23 14:00 | FK Pobeda v Rabotnicki Skopje | W | 0-1 |
Away History
| 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 |
| North Macedonia First League | 2023/05/07 15:00 | KF Shkupi Skopje v Shkendija Tetovo | W | 2-1 |
| North Macedonia First League | 2023/04/30 14:00 | FK Sileks v KF Shkupi Skopje | W | 0-2 |