The Macedonian Cup is the top knockout tournament in Macedonia. It was first introduced in 1992. Most succesful team in this competition is Vardar with 5 won titles and Sloga Jugomagnat follows with 3 titles. The winner of the cup gets a place in UEFA Europa League for the next season.
Macedonian Cup past winners.
1992/93 - Vardar - Pelister 1:0
1993/94 - Sileks - Pelister 1:1 (4:2 after penalties)
1994/95 - Vardar - Sileks 2:1
1995/96 - Sloga Jugomagnat - Vardar 0:0 (5:3 after penalties)
1996/97 - Sileks - Sloga Jugomagnat 4:1
1997/98 - Vardar - Sloga Jugomagnat 2:0
1998/99 - Vardar - Sloga Jugomagnat 2:0
1999/00 - Sloga Jugomagnat - Pobeda 6:0
2000/01 - Pelister - Sloga Jugomagnat 2:1
2001/02 - Pobeda - Cementarnica 55 3:1
2002/03 - Cementarnica 55 - Sloga Jugomagnat 4:4 (3:2 after penalties)
2003/04 - Sloga Jugomagnat - Napredok 1:0
2004/05 - Bashkimi - Madzari Solidarnost 2:1
2005/06 - Makedonija Gjorce Petrov - Shkendija 79 3:2
2006/07 - Vardar - Pobeda 2:1
2007/08 - Rabotnicki - Milano 2:0
2008/09 - Rabotnicki - Makedonija Gjorce Petrov 1:1 (6:5 after penalties)
2009/10 - Teteks - Rabotnicki 3:2
| Club | Titles |
| Vardar |
5 |
| Sloga Jugomagnat | 3 |
| Sileks |
2 |
| Rabotnicki |
2 |
| Pelister | 1 |
| Pobeda |
1 |
| Bashkimi |
1 |
| Makedonija Gjorce Petrov |
1 |
| Cementarnica 55 |
1 |
| Teteks |
1 |
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