[9] FK Skopje 1-3 KF Shkupi Skopje [1] 2021-12-05 12:00
Stadium: Zelezarnica Stadium Round: 16
Home Manager: Ljupco Markovski Away Manager: Goce Sedloski
Head to Head
| North Macedonia First League | 2021/08/28 14:00 | KF Shkupi Skopje v FK Skopje | L | 4-1 |
| North Macedonia First League | 2018/05/06 14:30 | FK Skopje v KF Shkupi Skopje | D | 1-1 |
| North Macedonia First League | 2018/03/18 13:00 | KF Shkupi Skopje v FK Skopje | W | 0-2 |
| North Macedonia First League | 2017/11/22 12:00 | FK Skopje v KF Shkupi Skopje | D | 0-0 |
| North Macedonia First League | 2017/09/20 13:30 | KF Shkupi Skopje v FK Skopje | L | 1-0 |
| Europe Friendlies | 2017/07/19 16:00 | FK Skopje v KF Shkupi Skopje | D | 0-0 |
| North Macedonia Second League | 2015/04/11 14:00 | KF Shkupi Skopje v FK Skopje | D | 0-0 |
| North Macedonia Second League | 2015/02/28 13:00 | FK Skopje v KF Shkupi Skopje | D | 1-1 |
Home History
| North Macedonia First League | 2021/11/28 12:00 | Pelister Bitola v FK Skopje | D | 0-0 |
| North Macedonia First League | 2021/11/20 12:00 | FK Skopje v Makedonija Gj. P | L | 1-2 |
| North Macedonia First League | 2021/11/06 12:00 | Bregalnica Stip v FK Skopje | L | 2-1 |
| North Macedonia First League | 2021/10/30 12:00 | FK Skopje v Renova Dzepciste | D | 0-0 |
| North Macedonia First League | 2021/10/24 12:00 | FK Skopje v Tikves Kavadarci | W | 2-1 |
| North Macedonia Cup | 2021/10/20 12:00 | Vardar Skopje v FK Skopje | L | 4-2 |
| North Macedonia First League | 2021/10/15 12:00 | Rabotnicki Skopje v FK Skopje | W | 0-1 |
| North Macedonia First League | 2021/10/02 13:00 | FK Skopje v Akademija Pandev | D | 0-0 |
Away History
| North Macedonia Cup | 2021/12/01 12:00 | Makedonija Gj. P v KF Shkupi Skopje | L | 4-1 |
| North Macedonia First League | 2021/11/28 12:00 | KF Shkupi Skopje v FC Struga Trim & Lum | W | 4-0 |
| North Macedonia First League | 2021/11/21 12:00 | KF Shkupi Skopje v Pelister Bitola | W | 5-0 |
| World Club Friendlies | 2021/11/11 11:00 | Besiktas v KF Shkupi Skopje | L | 3-0 |
| North Macedonia First League | 2021/11/06 12:00 | Makedonija Gj. P v KF Shkupi Skopje | L | 2-1 |
| North Macedonia First League | 2021/10/29 12:00 | KF Shkupi Skopje v Bregalnica Stip | W | 5-0 |
| North Macedonia First League | 2021/10/23 12:00 | KF Shkupi Skopje v Renova Dzepciste | W | 2-1 |
| North Macedonia Cup | 2021/10/20 12:00 | KF Shkupi Skopje v Tikves Kavadarci | W | 1-0 |