| 23. Round | 10/08/2016 | Bray Wanderers | - | Dundalk FC | 2:1 | ||||
| 24. Round | 19/08/2016 | Galway United | - | Bray Wanderers | 0:2 |  |
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| 25. Round | 27/08/2016 | Bray Wanderers | - | Derry City | 2:2 |  |
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| 22. Round | 30/08/2016 | Cork City | - | Bray Wanderers | 4:0 | ||||
| 20. Round | 06/09/2016 | St Patrick's Athletic | - | Bray Wanderers | 1:2 | |
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| 28. Round | 23/09/2016 | Wexford Youths | - | Bray Wanderers | 1:3 | ||||
| 30. Round | 07/10/2016 | Finn Harps | - | Bray Wanderers | 2:1 |
Ireland