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| 23.05.2009 | 20:30 | Blarney United | - | FC Carlow | 2:1 | |
| 20:30 | Cobh Ramblers | - | Carrigaline United | 1:2 | ||
| 20:30 | Salthill Devon | - | Newtown Rangers | 3:1 | ||
| 24.05.2009 | 15:00 | Fanad United | - | Ballymun United | 2:2 ap | |
| 15:00 | UC Dublin | - | Arklow Town | 1:2 | ||
| 15:30 | Crumlin United | - | Kildrum Tigers | 3:0 | ||
| 15:30 | Erris United | - | Cherry Orchard | 2:4 | ||
| 15:30 | Mayfield United | - | Castlebar Celtic | 3:2 | ||
| 16:00 | Bluebell United | - | Malahide United | 2:1 | ||
| 16:00 | Tralee Dynamos | - | St. Mary's AFC | 1:0 | ||
| match décisif | ||||||
|---|---|---|---|---|---|---|
| 31.05.2009 | 15:30 | Ballymun United | - | Fanad United | 3:0 | |
