FK Skopje 2-2 Metalurg Skopje
| 25.11.2009 | Metalurg Skopje | 2-2 | FK Skopje | |
| 28.10.2009 | FK Skopje | 0-0 | Metalurg Skopje | |
Makedonija GP 2-3 Teteks Tetovo
| 26.11.2009 | Teteks Tetovo | 3-0 | Makedonija GP | |
| 28.10.2009 | Makedonija GP | 2-0 | Teteks Tetovo | |
Pelister Bitola 3-2 Drita Bogovinje
| 25.11.2009 | Drita Bogovinje | 0-1 | Pelister Bitola | |
| 28.10.2009 | Pelister Bitola | 2-2 | Drita Bogovinje | |
Rabotnicki Skopje 5-0 Renova
| 25.11.2009 | Renova | 0-1 | Rabotnicki Skopje | |
| 28.10.2009 | Rabotnicki Skopje | 4-0 | Renova | |