| Time | Status | Match | FT | H1 | Stats | |
| 19/08/2019 17:00 |
(FT) | Novo Crnilishte Bregalnica Stip |
0 22 |
0 6 |
MF | ME | |
| 20/08/2019 17:00 |
(FT) | Pehchevo Pelister Bitola |
1 1 |
0 0 |
MF | ME | |
| 90 minutes[1-1], 120 minutes[1-1], Penalty Kicks[4-5] | ||||||
| 20/08/2019 17:00 |
(FT) | Ljuboten Tikves Kavadarci |
1 5 |
1 2 |
MF | ME | |
| 21/08/2019 17:00 |
(FT) | Fortuna Singelik Sileks |
0 4 |
0 2 |
MF | ME | |
| 21/08/2019 17:00 |
(FT) | Ohrid 2004 Belasica Strumica |
1 1 |
1 1 |
MF | ME | |
| 90 minutes[1-1], Penalty Kicks[5-4] | ||||||
| 21/08/2019 17:00 |
(FT) | Fk Rinija Gostivar FK Shkendija 79 |
1 4 |
0 1 |
MF | ME | |
| 21/08/2019 17:00 |
(FT) | Vlazrimi Kicevo Rabotnicki Skopje |
0 4 |
0 1 |
MF | ME | |
| 21/08/2019 17:00 |
(FT) | Prevalec Borec Veles |
0 4 |
0 2 |
MF | ME | |
| 21/08/2019 17:00 |
(FT) | Lokomotiva Skopje Struga Trim Lum |
1 5 |
0 0 |
MF | ME | |
| 21/08/2019 17:00 |
(FT) | Kozuv Renova Cepciste |
3 3 |
1 0 |
MF | ME | |
| 90 minutes[3-3], Penalty Kicks[5-6] | ||||||
| 21/08/2019 17:00 |
(FT) | FK Teteks Tetovo Korzo Prilep |
1 5 |
0 1 |
MF | ME | |
| 21/08/2019 17:00 |
(FT) | Kravari Labunishta |
1 4 |
0 2 |
MF | ME | |
| 21/08/2019 17:15 |
(FT) | Osogovo Pobeda Prilep |
1 0 |
1 0 |
MF | ME | |
| 28/08/2019 17:00 |
(FT) | Kamenica Sasa Vardar Skopje |
0 5 |
0 3 |
MF | ME | |