| Season | Winner | Runnerup | Score |
| 1992/93 | Vardar Skopje | Pelister Bitola | 1-0 |
| 1993/94 | Sileks Kratovo | Pelister Bitola | 1-1 [aet, 3-0 on pen] |
| 1994/95 | Vardar Skopje | Sileks Kratovo | 2-1 |
| 1995/96 | Sloga Jugomagnat | Vardar Skopje | 0-0 [aet, 4-2 on pen] |
| 1996/97 | Sileks Kratovo | Sloga Jugomagnat Skopje | 4-1 |
| 1997/98 | Vardar Skopje | Sloga Jugomagnat Skopje |
|
| Vardar Skopje | Sloga Jugomagnat Skopje |
2-0
|
|
| Sloga Jugomagnat Skopje | Pobeda Prilep |
5-0
|
Number
of Cups per Club (8 cups)
| Vardar Skopje |
4
|
| Sileks Kratovo |
2
|
| Sloga Jugomagnat |
2
|
| Pobeda Prilep |
1
|
Number of Finals per Club (16
finalists)
| Vardar Skopje | 5 |
| Sileks Kratovo | 3 |
| Sloga Jugomagnat Skopje | 4 |
| Pelister Bitola | 2 |
| Pobeda Prilep |
1
|
Number of Runnersup per Club
(8 runners up)
| Pelister Bitola | 2 |
| Sloga Jugomagnat Skopje | 4 |
| Sileks Kratovo | 1 |
| Vardar Skopje | 2 |
| Pobeda Prilep |
1
|