Vlaznimi Struga 1-2 Drita Bogovinje
| 30.09.2009 | Drita Bogovinje | 1-1 | Vlaznimi Struga | |
| 23.09.2009 | Vlaznimi Struga | 0-1 | Drita Bogovinje | |
FK Skopje 3-2 FK 11 Oktomvri
| 29.09.2009 | FK 11 Oktomvri | 1-0 | FK Skopje | |
| 22.09.2009 | FK Skopje | 3-1 | FK 11 Oktomvri | |
Pelister Bitola 2-0 FK Ohrid 2004*
| 30.09.2009 | FK Ohrid 2004* | P-P | Pelister Bitola | |
| 23.09.2009 | Pelister Bitola | 2-0 | FK Ohrid 2004* | |
Metalurg Skopje 1-1 Pobeda Prilep
| 30.09.2009 | Pobeda Prilep | 1-0/p.3-4 | Metalurg Skopje | |
| 23.09.2009 | Metalurg Skopje | 1-0 | Pobeda Prilep | |
FK Fortuna 0-6 Rabotnicki Skopje
| 30.09.2009 | Rabotnicki Skopje | P-P | FK Fortuna | |
| 23.09.2009 | FK Fortuna | 0-6 | Rabotnicki Skopje | |
Sileks Kratovo 2-3 Makedonija GP
| 30.09.2009 | Makedonija GP | 2-1 | Sileks Kratovo | |
| 23.09.2009 | Sileks Kratovo | 1-1 | Makedonija GP | |
Belasica Strumica 1-4 Teteks Tetovo
| 30.09.2009 | Teteks Tetovo | 1-0 | Belasica Strumica | |
| 23.09.2009 | Belasica Strumica | 1-3 | Teteks Tetovo | |