*Makedonija GP 2-1 Milano Kumanovo
| 06.05.2009 | Milano Kumanovo | 1-0 | Makedonija GP | |
| 08.04.2009 | Makedonija GP | 2-0 | Milano Kumanovo | |
*Rabotnicki Skopje 3-2 Shkendija'79
| 06.05.2009 | Shkendija'79 | 1-0 | Rabotnicki Skopje | |
| 08.04.2009 | Rabotnicki Skopje | 3-1 | Shkendija'79 | |