| 1. Round | 17/02/2023 | Treaty United | - | Bray Wanderers | 0:1 |  |
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| 2. Round | 24/02/2023 | Bray Wanderers | - | Kerry FC | 3:1 | ||||
| 3. Round | 03/03/2023 | Finn Harps | - | Bray Wanderers | 1:1 | |
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| 5. Round | 18/03/2023 | Waterford FC | - | Bray Wanderers | 2:2 | ||||
| 6. Round | 24/03/2023 | Bray Wanderers | - | Wexford FC | 3:2 | ||||
| 7. Round | 31/03/2023 | Cobh Ramblers | - | Bray Wanderers | 2:1 | |
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| 8. Round | 07/04/2023 | Bray Wanderers | - | Athlone Town | 1:0 | ||||
| 9. Round | 14/04/2023 | Galway United | - | Bray Wanderers | 6:0 | ||||
| 10. Round | 22/04/2023 | Longford Town | - | Bray Wanderers | 1:1 | ||||
| 13. Round | 05/05/2023 | Wexford FC | - | Bray Wanderers | 1:1 | ||||
| 14. Round | 12/05/2023 | Bray Wanderers | - | Finn Harps | 2:0 | ||||
| 15. Round | 19/05/2023 | Kerry FC | - | Bray Wanderers | 0:2 | |
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| 16. Round | 26/05/2023 | Bray Wanderers | - | Cobh Ramblers | 2:2 |  |
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| 20. Round | 23/06/2023 | Bray Wanderers | - | Kerry FC | 3:2 | ||||
| 21. Round | 30/06/2023 | Treaty United | - | Bray Wanderers | 1:1 | |
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| 22. Round | 07/07/2023 | Finn Harps | - | Bray Wanderers | 0:0 | ||||
| 23. Round | 14/07/2023 | Bray Wanderers | - | Wexford FC | 0:3 |
Ireland