Cup Winners
| Sezóna | Klub | |
| 2020/2021 |  | FK Sileks |
| 2018/2019 |  | AP Brera Strumica |
| 2017/2018 |  | KF Shkëndija 79 |
| 2016/2017 |  | FK Pelister |
| 2015/2016 | | KF Shkëndija 79 |
| 2012/2013 |  | FK Teteks |
| 2011/2012 |  | FK Renova |
| 2010/2011 |  | FK Metalurg |
| 2009/2010 | | FK Teteks |
| 2008/2009 |  | FK Rabotnički |
| 2007/2008 | | FK Rabotnički |
| 2006/2007 |  | FK Vardar |
| 2005/2006 |  | Makedonija GP |
| 2001/2002 |  | FK Pobeda |
| 2000/2001 | | FK Pelister |
| 1998/1999 | | FK Vardar |
| 1997/1998 | | FK Vardar |
| 1996/1997 | | FK Sileks |
| 1994/1995 | | FK Vardar |
| 1993/1994 | | FK Sileks |
| 1992/1993 | | FK Vardar |