Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 16.07.2009 |  | 2. Round First leg | Cherno Mo. - Iskra-Stal | CHE - ISK | 1:0 | |
| 06.08.2009 | | 3. Round 2nd leg | Cherno Mo. - PSV Eindhoven | CHE - PSV | 0:1 | 13.000 |
| 09.08.2009 |  | Matchday 1 | PSFC Chernomorets - Cherno Mo. | - CHE | 2:1 | 850 |
| 17.08.2009 | | Matchday 2 | PSFC Chernomorets - Lok Plovdiv | - LOK | 2:1 | 1.400 |
| 29.08.2009 | | Matchday 4 | PSFC Chernomorets - FK Sportist Svoge | - | 3:0 | 300 |
| 19.09.2009 | | Matchday 6 | PSFC Chernomorets - Pirin | - PIR | 2:1 | 700 |
| 03.10.2009 | | Matchday 8 | PSFC Chernomorets - PFC Montana | - MON | 1:1 | 1.200 |
| 24.10.2009 | | Matchday 10 | PSFC Chernomorets - Botev Plovdiv | - BOT | 2:0 | 750 |
| 07.11.2009 | | Matchday 12 | PSFC Chernomorets - Litex | - LOV | 1:2 | 3.900 |
| 29.11.2009 | | Matchday 14 | PSFC Chernomorets - Lokomotiv Sf | - LSO | 0:2 | 450 |