The Kup na Makedonija is North Macedonia's nationwide men's main cup. Its independent title line begins in 1992–93; earlier republic cup editions within Yugoslavia are excluded. The 2019–20 competition was abandoned because of the COVID-19 pandemic.
SeasonMacedonian CupRunner-upTrophy
2025/26Sileks KratovoKF Shkëndija
Decider: 1–0
2024/25Vardar SkopjeFC Struga Trim-Lum
Decider: 2–0
2023/24FK TikvešFK Voska Sport
Decider: 2–1
2022/23Makedonija Gjorče PetrovFC Struga Trim-Lum
Decider: 1–1 a.e.t.; 2–0 pens		—
2021/22Makedonija Gjorče PetrovSileks Kratovo
Decider: 0–0 a.e.t.; 4–3 pens		—
2020/21Sileks KratovoAkademija Pandev
Decider: 0–0 a.e.t.; 4–3 pens		—
2019/20Abandoned
The competition was abandoned because of the COVID-19 pandemic; no winner was determined.
2018/19Akademija PandevMakedonija Gjorče Petrov
Decider: 2–2 a.e.t.; 4–2 pens		—
2017/18KF ShkëndijaFK Pelister
Decider: 3–0		—
2016/17FK PelisterKF Shkëndija
Decider: 0–0 a.e.t.; 4–3 pens		—
2015/16KF ShkëndijaFK Rabotnički
Decider: 2–0		—
2014/15FK RabotničkiTeteks Tetovo
Decider: 2–1		—
2013/14FK RabotničkiMetalurg Skopje
Decider: 2–0		—
2012/13Teteks TetovoKF Shkëndija
Decider: 1–1 a.e.t.; 6–5 pens		—
2011/12FK RenovaFK Rabotnički
Decider: 3–1		—
2010/11Metalurg SkopjeTeteks Tetovo
Decider: 2–0		—
2009/10Teteks TetovoFK Rabotnički
Decider: 3–2		—
2008/09FK RabotničkiMakedonija Gjorče Petrov
Decider: 1–1 a.e.t.; 7–6 pens		—
2007/08FK RabotničkiMilano Kumanovo
Decider: 2–0		—
2006/07Vardar SkopjeFK Pobeda
Decider: 2–1		—
2005/06Makedonija Gjorče PetrovKF Shkëndija
Decider: 3–2		—
2004/05FK BashkimiFK Madžari Solidarnost
Decider: 2–1		—
2003/04FK Sloga JugomagnatFK Napredok
Decider: 1–0		—
2002/03FK Cementarnica 55FK Sloga Jugomagnat
Decider: 4–4 a.e.t.; 3–2 pens		—
2001/02FK PobedaFK Cementarnica 55
Decider: 3–1		—
2000/01FK PelisterFK Sloga Jugomagnat
Decider: 2–1		—
1999/00FK Sloga JugomagnatFK Pobeda
Decider: 6–0		—
1998/99Vardar SkopjeFK Sloga Jugomagnat
Decider: 2–0		—
1997/98Vardar SkopjeFK Sloga Jugomagnat
Decider: 2–0		—
1996/97Sileks KratovoFK Sloga Jugomagnat
Decider: 4–1		—
1995/96FK Sloga JugomagnatVardar Skopje
Decider: 0–0 a.e.t.; 5–3 pens		—
1994/95Vardar SkopjeSileks Kratovo
Decider: 2–1		—
1993/94Sileks KratovoFK Pelister
Decider: 1–1 a.e.t.; 3–1 pens		—
1992/93Vardar SkopjeFK Pelister
Decider: 1–0		—