| Time | Status | Match | FT | H1 | Stats |
| 03/10/2009 15:00 |
(FT) | Rabotnicki Skopje FK Makedonija |
1 1 |
1 1 |
MF | ME |
| 04/10/2009 15:00 |
(FT) | Renova Cepciste Sloga Jugomagnat |
3 1 |
2 0 |
MF | ME |
| 04/10/2009 15:00 |
(FT) | Metalurg Skopje Pobeda Prilep |
2 1 |
1 0 |
MF | ME |
| 04/10/2009 15:00 |
(FT) | Milano Vardar Skopje |
0 4 |
0 2 |
MF | ME |
| 04/10/2009 15:00 |
(FT) | Pelister Bitola FK Teteks Tetovo |
3 1 |
2 0 |
MF | ME |
| 04/10/2009 15:00 |
(FT) | Horizont Turnovo Sileks |
2 0 |
1 0 |
MF | ME |