1. Round
26/08/2009 Lepenec - FK Fortuna dnp
15:00 11 Oktomvri - Vardar Skopje 3:1
15:00 Mirce Acev - FK Renova 0:11
15:00 Bregalnica Delcevo - FK Pobeda 0:2
15:00 FK Belasica - Milano Kumanovo 3:1
15:00 FK Skopje - FK Sloga Jugomagnat 2:1
15:00 FK Ohrid - FK Turnovo 3:0
15:00 Dobrusevo - Sileks Kratovo 1:13
15:00 FK Vlazrimi 77 - FK Pelister 0:3
15:00 Babuna Martolci - Metalurg Skopje 1:3
15:00 FK Vlaznimi - FK Bregalnica Štip 4:3 pso
15:00 FK Kožuf - FK Rabotnički 0:5
15:00 FK Drita - Napredok Kičevo 1:0
15:00 Karbinci - Makedonija GP 1:4
09/09/2009 15:00 Prevalec - FK Teteks 0:4
Round of 16
22/09/2009 14:00 FK Skopje - 11 Oktomvri 3:1
23/09/2009 14:00 FK Pelister - FK Ohrid 2:0
14:00 Lokomotiva Skopje - FK Renova 0:3
14:00 Metalurg Skopje - FK Pobeda 1:0
14:00 FK Vlazrimi 77 - FK Drita 0:1
14:00 FK Belasica - FK Teteks 1:3
14:00 Sileks Kratovo - Makedonija GP 1:1
14:00 FK Fortuna - FK Rabotnički 0:6
30/09/2009 FK Ohrid - FK Pelister 0:3
FK Rabotnički - FK Fortuna 3:0
14:00 11 Oktomvri - FK Skopje 1:0
14:00 FK Renova - Lokomotiva Skopje 3:0
14:00 FK Pobeda - Metalurg Skopje 3:4 pso
14:00 FK Drita - FK Vlazrimi 77 1:1
14:00 FK Teteks - FK Belasica 1:0
14:00 Makedonija GP - Sileks Kratovo 2:1
Quarter-finals
28/10/2009 12:00 FK Pelister - FK Drita 2:2
12:00 FK Rabotnički - FK Renova 4:0
12:00 Makedonija GP - FK Teteks 2:0
12:00 FK Skopje - Metalurg Skopje 0:0
25/11/2009 12:00 FK Drita - FK Pelister 0:1
12:00 FK Renova - FK Rabotnički 0:1
12:00 Metalurg Skopje - FK Skopje 2:2
26/11/2009 12:00 FK Teteks - Makedonija GP 3:0
Semi-finals
07/04/2010 15:00 FK Pelister - FK Rabotnički 1:0
15:00 FK Teteks - FK Skopje 0:0
05/05/2010 15:30 FK Rabotnički - FK Pelister 5:4 pso
15:30 FK Skopje - FK Teteks 1:2
Final
26/05/2010 15:00 FK Teteks - FK Rabotnički 3:2
Kup na Makedonija
Kup na Makedonija