Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 13.03.2009 |  | Matchday 2 | Drogheda - Bray Wanderers | Dro - Bra | 0:0 | |
| 27.03.2009 | | Matchday 4 | Drogheda - Bohemians | Dro - BOH | 0:1 | |
| 03.04.2009 | | Matchday 5 | Drogheda - Shamrock | Dro - SHR | 2:2 | |
| 10.04.2009 | | Matchday 7 | Drogheda - Galway United | Dro - Gal | 0:1 | |
| 24.04.2009 | | Matchday 9 | Drogheda - Sligo Rovers | Dro - ROV | 0:0 | |
| 01.05.2009 | | Matchday 10 | Drogheda - Derry City | Dro - Der | 0:3 |