|
| Champions | # | Last | Cup Winners | # | Last | |||
|
|
|
|||||||
| 1 | FK Vardar Skopje | 10 | 2017 | 1 | FK Vardar Skopje | 5 | 2007 | |
| 2 | FC Shkupi Skopje | 4 | 2022 | 2 | FK Rabotnički Skopje | 4 | 2015 | |
| 3 | FK Rabotnički Skopje | 4 | 2014 | 3 | FC Shkupi Skopje | 3 | 2004 | |
| 4 | KF Shkėndija Tetovė | 4 | 2021 | 4 | FK Makedonija GP Skopje | 3 | 2023 | |
| 5 | Sileks FC Kratovo | 3 | 1998 | 5 | Sileks FC Kratovo | 3 | 2021 | |
| 6 | FK Pobeda Prilep | 2 | 2007 | 6 | KF Shkėndija Tetovė | 2 | 2018 | |
| 7 | FK Makedonija GP Skopje | 1 | 2009 | 7 | FK Pelister Bitola | 2 | 2017 | |
| 8 | KF Renova Depčite | 1 | 2010 | 8 | FK Teteks Tetovo | 2 | 2013 | |
| 9 | FC Struga Trim & Lum | 1 | 2023 | 9 | FK Pobeda Prilep | 1 | 2002 | |
| 10 | FK Akademija Pandev | 1 | 2019 | |||||
| 11 | FK Metalurg Skopje | 1 | 2011 | |||||
| 12 | FK Cementarnica-55 Skopje | 1 | 2003 | |||||
| 13 | KF Renova Depčite | 1 | 2012 | |||||
| 14 | KF Bashkimi Kumanovė | 1 | 2005 |
| Year | Champions | Runners-up | Third | Cup Winners |
 |
 |
 |
 |
|
| 2022/23 | FC Struga Trim & Lum | FC Shkupi Skopje | KF Shkėndija Tetovė | FK Makedonija GP Skopje |
| 2021/22 | FC Shkupi Skopje | FK Akademija Pandev | KF Shkėndija Tetovė | FK Makedonija GP Skopje |
| 2020/21 | KF Shkėndija Tetovė | FC Shkupi Skopje | FC Struga Trim & Lum | Sileks FC Kratovo |
| 2019/20 | league not finished | cup not finished | ||
| 2018/19 | KF Shkėndija Tetovė | FK Vardar Skopje | FK Akademija Pandev | FK Akademija Pandev |
| 2017/18 | KF Shkėndija Tetovė | FK Vardar Skopje | FK Rabotnički Skopje | KF Shkėndija Tetovė |
| 2016/17 | FK Vardar Skopje | KF Shkėndija Tetovė | FK Rabotnički Skopje | FK Pelister Bitola |
| 2015/16 | FK Vardar Skopje | KF Shkėndija Tetovė | Sileks FC Kratovo | KF Shkėndija Tetovė |
| 2014/15 | FK Vardar Skopje | FK Rabotnički Skopje | KF Shkėndija Tetovė | FK Rabotnički Skopje |
| 2013/14 | FK Rabotnički Skopje | FK Turnovo | FK Metalurg Skopje | FK Rabotnički Skopje |
| 2012/13 | FK Vardar Skopje | FK Metalurg Skopje | FK Turnovo | FK Teteks Tetovo |
| 2011/12 | FK Vardar Skopje | FK Metalurg Skopje | KF Shkėndija Tetovė | KF Renova Depčite |
| 2010/11 | KF Shkėndija Tetovė | FK Metalurg Skopje | KF Renova Depčite | FK Metalurg Skopje |
| 2009/10 | KF Renova Depčite | FK Rabotnički Skopje | FK Metalurg Skopje | FK Teteks Tetovo |
| 2008/09 | FK Makedonija GP Skopje | FC Milano Kumanovė | KF Renova Depčite | FK Rabotnički Skopje |
| 2007/08 | FK Rabotnički Skopje | FC Milano Kumanovė | FK Pelister Bitola | FK Rabotnički Skopje |
| 2006/07 | FK Pobeda Prilep | FK Rabotnički Skopje | FK Makedonija GP Skopje | FK Vardar Skopje |
| 2005/06 | FK Rabotnički Skopje | FK Makedonija GP Skopje | FK Vardar Skopje | FK Makedonija GP Skopje |
| 2004/05 | FK Rabotnički Skopje | FK Vardar Skopje | FK Pobeda Prilep | KF Bashkimi Kumanovė |
| 2003/04 | FK Pobeda Prilep | Sileks FC Kratovo | FK Vardar Skopje | FC Shkupi Skopje |
| 2002/03 | FK Vardar Skopje | FK Belasica Strumica | FK Pobeda Prilep | FK Cementarnica-55 Skopje |
| 2001/02 | FK Vardar Skopje | FK Belasica Strumica | FK Cementarnica-55 Skopje | FK Pobeda Prilep |
| 2000/01 | FC Shkupi Skopje | FK Vardar Skopje | FK Pobeda Prilep | FK Pelister Bitola |
| 1999/2000 | FC Shkupi Skopje | FK Pobeda Prilep | FK Rabotnički Skopje | FC Shkupi Skopje |
| 1998/99 | FC Shkupi Skopje | Sileks FC Kratovo | FK Pobeda Prilep | FK Vardar Skopje |
| 1997/98 | Sileks FC Kratovo | FC Shkupi Skopje | FK Makedonija GP Skopje | FK Vardar Skopje |
| 1996/97 | Sileks FC Kratovo | FK Pobeda Prilep | FC Shkupi Skopje | Sileks FC Kratovo |
| 1995/96 | Sileks FC Kratovo | FC Shkupi Skopje | FK Vardar Skopje | FC Shkupi Skopje |
| 1994/95 | FK Vardar Skopje | Sileks FC Kratovo | FC Shkupi Skopje | FK Vardar Skopje |
| 1993/94 | FK Vardar Skopje | Sileks FC Kratovo | FK Balkan 1921 Skopje | Sileks FC Kratovo |
| 1992/93 | FK Vardar Skopje | Sileks FC Kratovo | FK Balkan 1921 Skopje | FK Vardar Skopje |