| 2021/22 | FK Makedonija GP Skopje - FK Sileks Kratovo | 4 | - | 3 |
| 2020/21 | FK Sileks Kratovo - FK Akademija Pandev | 4 | - | 3 |
| 2018/19 | FK Akademija Pandev - FK Makedonija GP Skopje | 6 | - | 4 |
| 2017/18 | KF Skendija 79 Tetovo - FK Pelister Bitola | 3 | - | 0 |
| 2016/17 | FK Pelister Bitola - KF Skendija 79 Tetovo | 4 | - | 3 |
| 2015/16 | KF Skendija 79 Tetovo - FK Rabotnicki Skopje | 2 | - | 0 |
| 2014/15 | FK Rabotnicki Skopje - FK Teteks Tetovo | 2 | - | 1 |
| 2013/14 | FK Rabotnicki Skopje - FK Metalurg Skopje | 2 | - | 0 |
| 2012/13 | FK Teteks Tetovo - KF Skendija 79 Tetovo | 7 | - | 6 |
| FK Teteks Tetovo - KF Skendija 79 Tetovo | 0 | - | 0 |
| 2011/12 | FK Renova Cepciste - FK Rabotnicki Skopje | 3 | - | 1 |
| 2010/11 | FK Metalurg Skopje - FK Teteks Tetovo | 2 | - | 0 |
| 2009/10 | FK Teteks Tetovo - FK Rabotnicki Skopje | 3 | - | 2 |
| 2008/09 | FK Rabotnicki Skopje - FK Makedonija GP Skopje | 7 | - | 6 |
| 2007/08 | FK Rabotnicki Kometal Skopje - FK Milano Kumanovo | 2 | - | 0 |
| 2006/07 | FK Vardar Skopje - FK Pobeda Prileb | 2 | - | 1 |
| 2005/06 | FK Makedonija GP Skopje - KF Skendija 79 Tetovo | 3 | - | 2 |
| 2004/05 | FK Baskimi Kumanovo - Madzari Solidarnost Skopje | 2 | - | 1 |
| 2003/04 | Sloga Jugomagnat Skopje - FK Napredok Kicevo | 1 | - | 0 |
| 2002/03 | FK Cementarnica 55 Skopje - Sloga Jugomagnat Skopje | 7 | - | 6 |
| 2001/02 | FK Pobeda Prileb - FK Cementarnica 55 Skopje | 3 | - | 1 |
| 2000/01 | FK Pelister Bitola - Sloga Jugomagnat Skopje | 2 | - | 1 |
| 1999/00 | Sloga Jugomagnat Skopje - FK Pobeda Prileb | 6 | - | 0 |
| 1998/99 | FK Vardar Skopje - Sloga Jugomagnat Skopje | 2 | - | 0 |
| 1997/98 | FK Vardar Skopje - Sloga Jugomagnat Skopje | 2 | - | 0 |
| 1996/97 | FK Sileks Kratovo - Sloga Jugomagnat Skopje | 4 | - | 1 |
| 1995/96 | Sloga Jugomagnat Skopje - FK Vardar Skopje | 5 | - | 3 |
| 1994/95 | FK Vardar Skopje - FK Sileks Kratovo | 2 | - | 1 |
| 1993/94 | FK Sileks Kratovo - FK Pelister Bitola | 5 | - | 3 |
| 1992/93 | FK Vardar Skopje - FK Pelister Bitola | 1 | - | 0 |
