19.08.2019 17:00 FK Novo Crnilishte - FK Bregalnica Štip 0:22
20.08.2019 17:00 FK Ljuboten - GFK Tikvesh 1:5
17:00 FK Kit-Go Pehčevo - FK Pelister 4:5 i.E.
21.08.2019 17:00 FK Fortuna - Sileks Kratovo 0:4
17:00 FK Ohrid - FK Belasica 5:4 i.E.
17:00 FK Kravari - FK Labuništa 1:4
17:00 KF Gostivari - KF Shkëndija 79 1:4
17:00 FK Osogovo - FK Pobeda Junior 1:0
17:00 FK Vlazrimi 77 - FK Rabotnički 0:4
17:00 Prevalec - FK Borec 0:4
17:00 Lokomotiva Skopje - FC Struga 1:5
17:00 FK Kožuf - FK Renova 5:6 i.E.
17:00 FK Teteks - KF Shkupi 1:5
28.08.2019 17:00 Kamenica Sasa - Vardar Skopje 0:5
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