*Sileks Kratovo 2-0 Belasica Strumica
| 29.10.2008 | Belasica Strumica | 0-0 | Sileks Kratovo | |
| 22.10.2008 | Sileks Kratovo | 2-0 | Belasica Strumica | |
Drita Bogovinje 1-5 FK Miravci *
| 29.10.2008 | FK Miravci | 4-0 | Drita Bogovinje | |
| 22.10.2008 | Drita Bogovinje | 1-1 | FK Miravci | |
*Pelister Bitola 6-1 FK Turnovo
| 29.10.2008 | FK Turnovo | 1-2 | Pelister Bitola | |
| 22.10.2008 | Pelister Bitola | 4-0 | FK Turnovo | |
Pobeda Prilep 1-5 Makedonija GP *
| 29.10.2008 | Makedonija GP | 4-0 | Pobeda Prilep | |
| 22.10.2008 | Pobeda Prilep | 1-1 | Makedonija GP | |
Metalurg Skopje 0-1 Milano Kumanovo *
| 29.10.2008 | Milano Kumanovo | 0-0 | Metalurg Skopje | |
| 22.10.2008 | Metalurg Skopje | 0-1 | Milano Kumanovo | |
*Rabotnicki Skopje 3-0 Nov Milenium
| 29.10.2008 | Nov Milenium | 0-2 | Rabotnicki Skopje | |
| 22.10.2008 | Rabotnicki Skopje | 1-0 | Nov Milenium | |
Vardar Skopje 1-3 Renova *
| 30.10.2008 | Renova | 2-0 | Vardar Skopje | |
| 22.10.2008 | Vardar Skopje | 1-1 | Renova | |
*Shkendija'79 5-1 FK Ohrid 2004*
| 29.10.2008 | FK Ohrid 2004* | 1-2 | Shkendija'79 | |
| 22.10.2008 | Shkendija'79 | 3-0 | FK Ohrid 2004* | |