| 12. Ronde | 20.05.2014 | Dundalk FC | - | Drogheda United | 7:0 | ||||
| 14. Ronde | 23.05.2014 | Derry City | - | Drogheda United | 2:0 |  |
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| 15. Ronde | 30.05.2014 | Drogheda United | - | Limerick FC | 1:4 | ||||
| 20. Ronde | 02.06.2014 | St Patrick's Athletic | - | Drogheda United | 6:0 | ||||
| 16. Ronde | 13.06.2014 | Athlone Town | - | Drogheda United | 6:0 | ||||
| 17. Ronde | 27.06.2014 | Drogheda United | - | Sligo Rovers | 1:2 | ||||
| 19. Ronde | 11.07.2014 | Drogheda United | - | Cork City | 0:1 | ||||
| 21. Ronde | 25.07.2014 | Shamrock Rovers | - | Drogheda United | 0:1 |
Ierland