| 23. Round | 14/07/2023 | Bray Wanderers | - | Wexford FC | 0:3 |  |
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| 24. Round | 28/07/2023 | Galway United | - | Bray Wanderers | 3:0 | |
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| 25. Round | 04/08/2023 | Bray Wanderers | - | Athlone Town | 2:2 | ||||
| 26. Round | 07/08/2023 | Bray Wanderers | - | Longford Town | 2:4 | |
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| 27. Round | 11/08/2023 | Cobh Ramblers | - | Bray Wanderers | 3:3 | |
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| 28. Round | 25/08/2023 | Bray Wanderers | - | Waterford FC | 0:1 | |
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| 29. Round | 01/09/2023 | Kerry FC | - | Bray Wanderers | 1:3 | ||||
| 30. Round | 08/09/2023 | Bray Wanderers | - | Galway United | 1:4 | |
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| 31. Round | 15/09/2023 | Bray Wanderers | - | Treaty United | 2:2 | ||||
| 32. Round | 22/09/2023 | Wexford FC | - | Bray Wanderers | 2:1 |
Ireland