| 1. Round | 24/02/2017 | Galway United | - | Drogheda United | 0:1 |  |
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| 2. Round | 03/03/2017 | Drogheda United | - | St Patrick's Athletic | 2:0 | ||||
| 3. Round | 10/03/2017 | Drogheda United | - | Cork City | 1:4 | ||||
| 4. Round | 13/03/2017 | Bray Wanderers | - | Drogheda United | 2:1 | ||||
| 5. Round | 18/03/2017 | Derry City | - | Drogheda United | 4:0 | ||||
| 6. Round | 25/03/2017 | Drogheda United | - | Bohemian FC | 0:1 | ||||
| 7. Round | 31/03/2017 | Dundalk FC | - | Drogheda United | 3:1 | ||||
| 8. Round | 07/04/2017 | Drogheda United | - | Shamrock Rovers | 2:1 |  |
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| 9. Round | 15/04/2017 | Limerick FC | - | Drogheda United | 3:0 | |
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| 10. Round | 21/04/2017 | Finn Harps | - | Drogheda United | 0:2 | ||||
| 11. Round | 28/04/2017 | Drogheda United | - | Sligo Rovers | 1:1 | |
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| 14. Round | 19/05/2017 | Cork City | - | Drogheda United | 5:0 | |
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| 16. Round | 26/05/2017 | Drogheda United | - | Derry City | 0:0 | ||||
| 18. Round | 16/06/2017 | Drogheda United | - | Dundalk FC | 0:6 | |
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| 20. Round | 30/06/2017 | Drogheda United | - | Limerick FC | 0:2 | ||||
| 21. Round | 07/07/2017 | Drogheda United | - | Finn Harps | 0:2 |
Ireland