| 1. Round | 05/03/2016 | Bray Wanderers | - | Dundalk FC | 1:3 |  |
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| 2. Round | 11/03/2016 | Galway United | - | Bray Wanderers | 4:0 | ||||
| 4. Round | 19/03/2016 | Longford Town | - | Bray Wanderers | 1:1 |  |
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| 5. Round | 26/03/2016 | Bray Wanderers | - | Sligo Rovers | 4:0 | ||||
| 6. Round | 01/04/2016 | Wexford Youths | - | Bray Wanderers | 2:0 | ||||
| 7. Round | 09/04/2016 | Bray Wanderers | - | Bohemian FC | 0:2 | ||||
| 12. Round | 10/05/2016 | Dundalk FC | - | Bray Wanderers | 1:0 | ||||
| 13. Round | 14/05/2016 | Bray Wanderers | - | Galway United | 1:2 | ||||
| 14. Round | 29/05/2016 | Derry City | - | Bray Wanderers | 2:0 | ||||
| 15. Round | 03/06/2016 | Bray Wanderers | - | Longford Town | 0:0 | ||||
| 16. Round | 24/06/2016 | Sligo Rovers | - | Bray Wanderers | 0:0 | ||||
| 17. Round | 02/07/2016 | Bray Wanderers | - | Wexford Youths | 3:0 | |
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| 21. Round | 29/07/2016 | Bray Wanderers | - | Shamrock Rovers | 1:1 | ||||
| 30. Round | 07/10/2016 | Finn Harps | - | Bray Wanderers | 2:1 | |
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| 31. Round | 14/10/2016 | Bray Wanderers | - | St Patrick's Athletic | 2:1 | ||||
| 32. Round | 21/10/2016 | Shamrock Rovers | - | Bray Wanderers | 0:0 | ||||
| 33. Round | 28/10/2016 | Bray Wanderers | - | Cork City | 4:1 |
Ireland