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1/16-finals
1/8-finals
Quarter-finals
Semi-finals
2019/20
1/16-finals
| 1 | Shkupi | Teteks | 5 : 1 |
| 2 | Fortuna Skopje | Sileks | 0 : 4 |
| 3 | Brera Strumica | Bye | |
| 4 | Pobeda | Osogovo | 0 : 1 |
| 5 | Bregalnica Stip | Novo Crnilishte | 22 : 0 |
| 6 | Bye | Makedonija GP | |
| 7 | Labunishta | Kravari | 4 : 1 |
| 8 | Belasica | Ohrid | 1 : 2 |
| 9 | Vardar | Sasa | 5 : 0 |
| 10 | KF Gostivar | Shkendija | 1 : 4 |
| 11 | Pelister | FK Pehchevo | 2 : 1 |
| 12 | Vellazerimi | Rabotnicki | 0 : 4 |
| 13 | Borec | Prevalec | 4 : 0 |
| 14 | Lok. Skopje | Struga | 1 : 5 |
| 15 | Tikves | Ljuboten | 5 : 1 |
| 16 | Kozuf Gevgelija | Renova | 3 : 4 |
1/8-finals
| 1 | Shkupi | Sileks | 1 : 1, 0 : 0 |
| 2 | Brera Strumica | Osogovo | 4 : 1, 3 : 0 |
| 3 | Bregalnica Stip | Makedonija GP | 0 : 0, 1 : 0 |
| 4 | Labunishta | Ohrid | 3 : 2, 2 : 0 |
| 5 | Vardar | Shkendija | 0 : 1, 2 : 2 |
| 6 | Pelister | Rabotnicki | 0 : 4, 1 : 1 |
| 7 | Borec | Struga | 0 : 1, 0 : 0 |
| 8 | Tikves | Renova | 1 : 1, 0 : 2 |
Quarter-finals
| 1 | Shkupi | Brera Strumica | 1 : 1, 0 : 1 |
| 2 | Bregalnica Stip | Labunishta | 4 : 1, 1 : 0 |
| 3 | Shkendija | Rabotnicki | 2 : 2, 1 : 1 |
| 4 | Struga | Renova | 2 : 1, 0 : 0 |
Semi-finals
| 1 | Brera Strumica | Bregalnica Stip | |
| 2 | Shkendija | Struga |
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