[3] Akademija Pandev 2-0 FK Borec [9] 2019-08-25 15:00
Stadium: Kukus Stadium Round: 3
Home Manager: Jugoslav Trencovski Away Manager: Gorazd Mihajlov
Home History
| North Macedonia First League | 2019/08/18 15:00 | Makedonija Gj. P v Akademija Pandev | D | 0-0 |
| North Macedonia First League | 2019/08/10 15:30 | Akademija Pandev v Shkendija Tetovo | W | 1-0 |
| Europe Friendlies | 2019/07/28 16:00 | Akademija Pandev v Bregalnica Stip | W | 3-1 |
| UEFA Europa League Qualifying | 2019/07/18 17:00 | Zrinjski Mostar v Akademija Pandev | L | 3-0 |
| UEFA Europa League Qualifying | 2019/07/11 17:00 | Akademija Pandev v Zrinjski Mostar | L | 0-3 |
| Europe Friendlies | 2019/06/27 13:00 | Teuta Durres v Akademija Pandev | L | 4-1 |
| Europe Friendlies | 2019/06/25 15:45 | Akademija Pandev v FC Academica Clinceni | D | 1-1 |
| Europe Friendlies | 2019/06/24 12:58 | Slavia Sofia v Akademija Pandev | L | 3-2 |
Away History
| North Macedonia Cup | 2019/08/21 15:00 | FK Prevalec v FK Borec | W | 0-4 |
| North Macedonia First League | 2019/08/18 15:00 | FK Borec v Vardar Skopje | D | 0-0 |
| North Macedonia First League | 2019/08/10 15:30 | KF Shkupi Skopje v FK Borec | L | 2-0 |
| Europe Friendlies | 2019/08/04 17:00 | Bregalnica Stip v FK Borec | D | 2-2 |
| Europe Friendlies | 2019/07/31 16:11 | FK Kadino v FK Borec | L | 1-0 |
| Europe Friendlies | 2019/07/27 15:00 | FK Lokomotive v FK Borec | W | 1-3 |
| Europe Friendlies | 2019/07/12 07:36 | Septemvri Sofia v FK Borec | D | 1-1 |
| Europe Friendlies | 2019/07/06 15:42 | Rabotnicki Skopje v FK Borec | W | 0-5 |