Finals
| Season | Winner | Res. | Runner-up |
|---|---|---|---|
| 1992-93 | Vardar | 1–0 | Pelister |
| 1993-94 | Sileks | 1–1 (4-2 pen) | Pelister |
| 1994-95 | Vardar | 2–1 | Sileks |
| 1995-96 | Sloga Jugomagnat | 0–0 (5-3 pen) | Vardar |
| 1996-97 | Sileks | 4–1 | Sloga Jugomagnat |
| 1997-98 | Vardar | 2–0 | Sloga Jugomagnat |
| 1998-99 | Vardar | 2–0 | Sloga Jugomagnat |
| 1999-00 | Sloga Jugomagnat | 6–0 | Pobeda |
| 2000-01 | Pelister | 2–1 | Sloga Jugomagnat |
| 2001-02 | Pobeda | 3–1 | Cementarnica 55 |
| 2002-03 | Cementarnica 55 | 4–4 (3-2 pen) | Sloga Jugomagnat |
| 2003-04 | Sloga Jugomagnat | 1–0 | Napredok |
| 2004-05 | Baškimi | 2–1 | Madžari Solidarnost |
| 2005-06 | Makedonija Gjorče Petrov | 3–2 | Škendija 79 |
| 2006-07 | Vardar | 2–1 | Pobeda |
| 2007-08 | Rabotnički Kometal | 2–0 | Milano |
| 2008-09 | Rabotnički | 1–1 (6-5 pen) | Makedonija Gjorče Petrov |
| 2009-10 | Teteks | 3–2 | Rabotnički |
| 2010-11 | Metalurg | 2–0 | Teteks |
| 2011-12 | Renova | 3–1 | Rabotnički |
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