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| 26/08/2009 | Lepenec | - | FK Fortuna | dnp | ||
| 15:00 | 11 Oktomvri | - | Vardar Skopje | 3:1 | ||
| 15:00 | Mirce Acev | - | FK Renova | 0:11 | ||
| 15:00 | Bregalnica Delcevo | - | FK Pobeda | 0:2 | ||
| 15:00 | FK Belasica | - | Milano Kumanovo | 3:1 | ||
| 15:00 | FK Skopje | - | FK Sloga Jugomagnat | 2:1 | ||
| 15:00 | FK Ohrid | - | FK Turnovo | 3:0 | ||
| 15:00 | Dobrusevo | - | Sileks Kratovo | 1:13 | ||
| 15:00 | FK Vlazrimi 77 | - | FK Pelister | 0:3 | ||
| 15:00 | Babuna Martolci | - | Metalurg Skopje | 1:3 | ||
| 15:00 | FK Vlaznimi | - | FK Bregalnica Štip | 4:3 pso | ||
| 15:00 | FK Kožuf | - | FK Rabotnički | 0:5 | ||
| 15:00 | FK Drita | - | Napredok Kičevo | 1:0 | ||
| 15:00 | FK Karbinci | - | Makedonija GP | 1:4 | ||
| 09/09/2009 | 15:00 | Prevalec | - | FK Teteks | 0:4 |
