| Time | Status | Match | FT | H1 | Stats |
| 01/08/2009 17:00 |
(FT) | FK Teteks Tetovo FK Makedonija |
2 2 |
1 0 |
MF | ME |
| 01/08/2009 17:00 |
(FT) | Milano Renova Cepciste |
0 2 |
0 1 |
MF | ME |
| 01/08/2009 17:00 |
(FT) | Sileks Vardar Skopje |
1 1 |
0 0 |
MF | ME |
| 01/08/2009 17:00 |
(FT) | Pelister Bitola Sloga Jugomagnat |
0 0 |
0 0 |
MF | ME |
| 02/08/2009 17:00 |
(FT) | Rabotnicki Skopje Metalurg Skopje |
1 1 |
1 0 |
MF | ME |
| 03/08/2009 17:00 |
(FT) | Horizont Turnovo Pobeda Prilep |
3 1 |
2 0 |
MF | ME |