| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 26.08.2009 | 1. Round | 1. Round | H | ![]() | Napredok | W | 1:0 |
| 23.09.2009 | Round of 16 First leg | Rd of 16 First leg | A | ![]() | Vlazrimi | W | 1:0 |
| 30.09.2009 | Round of 16 2nd leg | Rd of 16 2nd leg | H | ![]() | Vlazrimi | D | 1:1 |
| 28.10.2009 | Quarter-finals First leg | Quarter-Finals First leg | A | ![]() | FK Pelister | D | 2:2 |
| 25.11.2009 | Quarter-finals 2nd leg | Quarter-Finals 2nd leg | H | ![]() | FK Pelister | L | 0:1 |
FK Drita



