FK Miravci 1-4 Makedonija GP
| 06.12.2008 | Makedonija GP | 3-0 | FK Miravci | |
| 26.11.2008 | FK Miravci | 1-1 | Makedonija GP | |
Pelister Bitola 3-4 Shkendija'79 *
| 10.12.2008 | Shkendija'79 | 3-0 | Pelister Bitola | |
| 26.11.2008 | Pelister Bitola | 3-1 | Shkendija'79 | |
Renova 0-1 Rabotnicki Skopje *
| 10.12.2008 | Rabotnicki Skopje | 1-0 | Renova | |
| 26.11.2008 | Renova | 0-0 | Rabotnicki Skopje | |
Sileks Kratovo 1-4 Milano Kumanovo *
| 10.12.2008 | Milano Kumanovo | 2-1 | Sileks Kratovo | |
| 26.11.2008 | Sileks Kratovo | 0-2 | Milano Kumanovo | |