| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 24.05.2009 | 2. Round | 2. Rd | H | ![]() | Arklow Town | L | 1:2 |
| 12.06.2009 | 3. Round | 3. Rd | H | ![]() | Arklow Town | W | 3:1 |
| 15.08.2009 | Round of 16 | Rd of 16 | A | ![]() | Shamrock | L | 1:3 |
| Date | Round | Round | H/A | Res. | |||
| 14.04.2009 | 1. Round | 1. Round | A | ![]() | Tullamore Town | W | 2:0 |
| 05.05.2009 | Round of 16 | Rd of 16 | A | ![]() | Athlone Town | W | 1:0 |
| 18.05.2009 | Quarter-finals | Quarter-Finals | A | ![]() | Galway United | W | 2:0 |
| 04.08.2009 | Semi-finals | Semi-Final | H | ![]() | Waterford | L | 1:3 |
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