Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 06.03.2009 |  | Matchday 1 | Derry City - Drogheda | Der - Dro | 1:0 | |
| 20.03.2009 | | Matchday 3 | Derry City - Cork City | Der - Cor | 2:1 | |
| 03.04.2009 | | Matchday 5 | Derry City - Galway United | Der - Gal | 1:1 | |
| 10.04.2009 | | Matchday 7 | Derry City - Sligo Rovers | Der - ROV | 1:2 | |
| 24.04.2009 | | Matchday 9 | Derry City - Dundalk | Der - Dun | 0:1 | |
| 23.07.2009 |  | 2. Round 2nd leg | Derry City - Skonto | Der - SKO | 1:0 | |
| 06.08.2009 | | 3. Round 2nd leg | Derry City - CSKA Sofia | Der - SOF | 1:1 | 3.000 |