| Time | Status | Match | FT | H1 | Stats |
| 18/09/2009 15:30 |
(FT) | Rabotnicki Skopje Sileks |
1 1 |
1 0 |
MF | ME |
| 19/09/2009 15:30 |
(FT) | Renova Cepciste Pobeda Prilep |
2 1 |
1 1 |
MF | ME |
| 19/09/2009 15:30 |
(FT) | Milano FK Teteks Tetovo |
1 5 |
0 1 |
MF | ME |
| 20/09/2009 15:30 |
(FT) | Metalurg Skopje FK Makedonija |
0 0 |
0 0 |
MF | ME |
| 20/09/2009 15:30 |
(FT) | Pelister Bitola Horizont Turnovo |
1 2 |
0 0 |
MF | ME |
| 21/09/2009 15:30 |
(FT) | Sloga Jugomagnat Vardar Skopje |
1 0 |
0 0 |
MF | ME |