Macedonian Cup 2008/09
| 1/16 final | 17.09.2008 |
| Fortuna – Pobeda | 2:3 |
| Ohrid – Bashkimi | (Bashkimi quits) |
| Bregalnica Shtip – Horizont Turnovo | (Bregalnica Shtip quits) |
| Vardino – Milano | 0:4 |
| Karaorman – Belasica | (Karaorman quits) |
| Gostivar – Miravci | (Gostivar quits) |
| Teteks – Makedonija Gjorche Petrov | 0:1 |
| Lokomotiva – Rabotnichki | 0:2 |
| Nov Milenium – Cementarnica 55 | 1:0 |
| Kravari – Shkendija HB | 0:4 |
| Babuna – Vardar | 0:3 |
| Sloga Jugomagnat – Renova | 2:4 |
| 11 Oktomvri – Metalurg | 0:1 |
| Vlazrimi – Sileks | 0:2 |
| Kozhuf – Pelister | 1:4 |
| Drita – Napredok | 2:1 |
| 1/8 final 2nd leg | 29.10.2008 |
| Milano – Metalurg | 0:0 |
| Renova – Vardar | 2:0 |
| Nov Milenium – Rabotnichki | 0:2 |
| Miravci – Drita | 4:0 |
| Belasica – Sileks | 0:0 |
| Horizont Turnovo – Pelister | 1:2 |
| Makedonija GjP – Pobeda | 4:0 |
| Ohrid – Shkendija | 1:2 |
| 1/8 final | 22.10.2008 |
| Metalurg – Milano | 0:1 |
| Vardar – Renova | 1:1 |
| Rabotnichki – Nov Milenium | 1:0 |
| Drita – Miravci | 1:1 |
| Sileks – Belasica | 2:0 |
| Pelister – Horizont Turnovo | 4:0 |
| Pobeda – Makedonija GjP | 1:1 |
| Shkendija – Ohrid | 3:0 |
| 1/4 final 2nd leg | 10.12.2008 |
| Shkendija – Pelister | 3:0 |
| Rabotnichki – Renova | 1:0 |
| Milano – Sileks | 2:1 |
| Makedonija GjP – Miravci | 3:0 |
| 1/4 final | 26.11.2008 |
| Pelister – Shkendija | 3:1 |
| Renova – Rabotnichki | 0:0 |
| Sileks – Milano | 0:2 |
| Miravci – Makedonija GjP | 1:1 |
| 1/2 final 2nd leg | 06.05.2009 |
| Shkendija – Rabotnichki | 1:0 |
| Milano – Makedonija GjP | 1:0 |
| 1/2 final | 08.04.2009 |
| Rabotnichki – Shkendija | 3:1 |
| Makedonija GjP – Milano | 2:0 |
| Final match | 24.05.2009 |
| Rabotnichki – Makedonija Gjorche Petrov | 1:1 (6:5 p.s.o) |
| WINNER: RABOTNICKI |