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| 20/05/2016 | 19:45 | Dundalk FC | - | Shelbourne FC | 2:0 (1:0) | |
| 19:45 | Bohemian FC | - | Galway United | 2:0 (1:0) | ||
| 19:45 | Derry City | - | Drogheda United | 1:1 (0:1) | ||
| 19:45 | UC Dublin | - | Bray Wanderers | 4:3 (3:0) | ||
| 19:45 | Waterford United | - | Longford Town | 0:2 (0:2) | ||
| 19:45 | Cork City | - | St. Peter's | 4:0 (3:0) | ||
| 20:00 | Firhouse Clover | - | Wexford Youths | 0:3 (0:0) | ||
| 20:00 | Shamrock Rovers | - | Midleton FC | 4:0 (1:0) | ||
| 21/05/2016 | 14:00 | Bluebell United | - | Limerick FC | 2:5 (0:2) | |
| 14:00 | Ringmahon Rangers | - | Glebe North | 2:1 (0:0) | ||
| 14:30 | Cobh Ramblers | - | Cherry Orchard | 2:1 (1:1) | ||
| 15:00 | St Patrick's Athletic | - | Pike Rovers | 8:0 (4:0) | ||
| 19:45 | Athlone Town | - | Letterkenny Rovers | 0:0 (0:0) | ||
| 19:45 | Sligo Rovers | - | Cabinteely FC | 3:0 (2:0) | ||
| 20:00 | Finn Harps | - | Crumlin United | 0:1 (0:0) | ||
| 22/05/2016 | 15:00 | Janesboro FC | - | Sheriff YC | 2:1 (0:1) | |
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 24/05/2016 | 18:00 | Letterkenny Rovers | - | Athlone Town | 0:1 (0:0, 0:0) aet | |
| 19:45 | Drogheda United | - | Derry City | 1:2 (1:1) | ||
