2025/26 2024/25 2023/24 2022/23 2021/22 2020/21 2019/20 2018/19 2017/18 2016/17 2015/16 2014/15 2013/14 2012/13 2011/12 2010/11 2009/10
1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2018/19
1/16-finals
| 1 | Belasica | Vellazerimi | 4 : 0 |
| 2 | Osogovo | Pelister | 0 : 1 |
| 3 | FK Skopje | Vardar Negotino | 3 : 1 |
| 4 | Bratstvo-Vlaznimi | Sileks | 0 : 7 |
| 5 | Rabotnicki | Fortuna Skopje | 6 : 0 |
| 6 | Renova | Tikves | 1 : 2 |
| 7 | Vardar | Vardari Forino | 4 : 0 |
| 8 | Prevalec | Makedonija GP | 0 : 2 |
| 9 | Brera Strumica | Labunishta | 3 : 1 |
| 10 | Poeshevo | Bregalnica Stip | 0 : 8 |
| 12 | Borec | FK Korab | 0 : 1 |
| 13 | Shkendija | Kozuf Gevgelija | 2 : 0 |
| 14 | Shkupi | FK Pehchevo | 0 : 2 |
| 15 | KF Gostivar | Teteks | 2 : 1 |
| 16 | Struga | Pobeda | 1 : 2 |
1/8-finals
| 1 | Belasica | Pelister | 3 : 1, 2 : 0 |
| 2 | FK Skopje | Sileks | 1 : 2, 0 : 2 |
| 3 | Rabotnicki | Tikves | 1 : 1, 1 : 0 |
| 4 | Vardar | Makedonija GP | 1 : 2, 1 : 1 |
| 5 | Brera Strumica | Bregalnica Stip | 0 : 1, 6 : 2 |
| 6 | Bye | FK Korab | |
| 7 | Shkendija | FK Pehchevo | 5 : 0, 2 : 0 |
| 8 | KF Gostivar | Pobeda | 1 : 4, 1 : 2 |
Quarter-finals
| 1 | Belasica | Sileks | 2 : 0, 2 : 0 |
| 2 | Rabotnicki | Makedonija GP | 0 : 1, 0 : 1 |
| 3 | Brera Strumica | FK Korab | 6 : 1, 3 : 1 |
| 4 | Shkendija | Pobeda | 0 : 2, 0 : 1 |
Semi-finals
| 1 | Belasica | Makedonija GP | 0 : 1, 0 : 1 |
| 2 | Brera Strumica | Pobeda | 3 : 1, 3 : 1 |
Final
| 1 | Makedonija GP | Brera Strumica | 2 : 3 |
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