[4] Bregalnica Stip 2-0 KF Shkupi Skopje [5] 2022-09-04 14:00
Stadium: City Stadium Round: 6
Home Manager: Marjan Sekulovski Away Manager: Goce Sedloski
Head to Head
| North Macedonia First League | 2022/04/30 15:00 | Bregalnica Stip v KF Shkupi Skopje | W | 4-1 |
| North Macedonia First League | 2021/10/29 12:00 | KF Shkupi Skopje v Bregalnica Stip | L | 5-0 |
| North Macedonia First League | 2021/08/08 15:30 | Bregalnica Stip v KF Shkupi Skopje | D | 0-0 |
| North Macedonia First League | 2017/05/21 14:30 | KF Shkupi Skopje v Bregalnica Stip | L | 3-0 |
| North Macedonia First League | 2017/04/05 14:00 | Bregalnica Stip v KF Shkupi Skopje | W | 3-0 |
| North Macedonia First League | 2016/11/27 12:00 | KF Shkupi Skopje v Bregalnica Stip | D | 1-1 |
| North Macedonia First League | 2016/09/25 13:30 | Bregalnica Stip v KF Shkupi Skopje | W | 1-0 |
| North Macedonia First League | 2016/04/24 14:00 | Bregalnica Stip v KF Shkupi Skopje | W | 2-0 |
Home History
| North Macedonia First League | 2022/08/28 14:00 | Bregalnica Stip v Makedonija Gj. P | W | 1-0 |
| North Macedonia First League | 2022/08/21 15:00 | Tikves Kavadarci v Bregalnica Stip | D | 1-1 |
| North Macedonia First League | 2022/08/14 15:00 | Bregalnica Stip v FC Struga Trim & Lum | L | 0-1 |
| North Macedonia First League | 2022/08/07 15:30 | Akademija Pandev v Bregalnica Stip | W | 1-2 |
| Europe Friendlies | 2022/07/27 16:00 | Bregalnica Stip v FK Kozuf Gevgelija | W | 4-0 |
| Europe Friendlies | 2022/07/18 08:00 | CSA Steaua Bucuresti v Bregalnica Stip | D | 0-0 |
| Club Friendly List | 2022/07/14 15:30 | Bregalnica Stip v FK Trayal Krusevac | W | 2-0 |
| Europe Friendlies | 2022/07/10 15:00 | Bregalnica Stip v Rabotnicki Skopje | D | 0-0 |
Away History
| North Macedonia First League | 2022/08/31 14:00 | KF Shkupi Skopje v FK Pobeda | D | 1-1 |
| North Macedonia First League | 2022/08/28 14:00 | FK Skopje v KF Shkupi Skopje | W | 0-2 |
| UEFA Conference League Qualifying | 2022/08/25 18:00 | KF Ballkani v KF Shkupi Skopje | L | 1-0 |
| UEFA Conference League Qualifying | 2022/08/18 19:00 | KF Shkupi Skopje v KF Ballkani | L | 1-2 |
| North Macedonia First League | 2022/08/13 15:00 | KF Shkupi Skopje v Makedonija Gj. P | W | 2-1 |
| UEFA Europa League Qualifying | 2022/08/09 19:00 | KF Shkupi Skopje v Shamrock Rovers | L | 1-2 |
| UEFA Europa League Qualifying | 2022/08/04 19:00 | Shamrock Rovers v KF Shkupi Skopje | L | 3-1 |
| UEFA Champions League Qualifying | 2022/07/26 19:00 | KF Shkupi Skopje v Dinamo Zagreb | L | 0-1 |