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| 23.08.2009 | 16:00 | FK Pobeda | - | Makedonija GP | ann. | |
| 16:00 | Metalurg Skopje | - | Sileks Kratovo | 2:2 | ||
| 16:00 | Milano Kumanovo | - | FK Turnovo | 0:2 | ||
| 16:00 | FK Rabotnički | - | FK Pelister | 3:0 | ||
| 30.08.2009 | 16:00 | FK Renova | - | Vardar Skopje | 3:2 | |
| 16:00 | FK Sloga Jugomagnat | - | FK Teteks | 1:0 |
| » Classement | équipe recevante | à l'extérieur | Premier tour | Second tour |
| # | Équipe | M. | G. | N. | P. | Buts | Diff. | Pts. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
FK Rabotnički | 4 | 3 | 1 | 0 | 8:2 | 6 | 10 |
| 2 |
|
FK Renova | 4 | 3 | 0 | 1 | 7:4 | 3 | 9 |
| 3 |
|
FK Pelister | 4 | 2 | 1 | 1 | 5:5 | 0 | 7 |
| 4 |
|
Sileks Kratovo | 3 | 1 | 2 | 0 | 5:4 | 1 | 5 |
| 5 |
|
Metalurg Skopje | 4 | 0 | 3 | 1 | 5:6 | -1 | 3 |
| 6 |
|
FK Turnovo | 3 | 1 | 2 | 0 | 4:2 | 2 | 2 |
| 7 |
|
FK Teteks | 3 | 0 | 1 | 2 | 3:6 | -3 | 1 |
| 8 |
|
Vardar Skopje | 4 | 1 | 1 | 2 | 6:10 | -4 | 1 |
| 9 |
|
Milano Kumanovo | 4 | 0 | 0 | 4 | 1:9 | -8 | 0 |
| 10 |
|
FK Pobeda | 0 | 0 | 0 | 0 | 0:0 | 0 | 0 |
| 11 |
|
FK Sloga Jugomagnat | 4 | 1 | 2 | 1 | 3:3 | 0 | -6 |
| 12 |
|
Makedonija GP | 3 | 1 | 1 | 1 | 7:3 | 4 | -15 |
| Champions League Quali. | |
| Europa League | |
| Relégation | |
| Relégation |
