| 4. Round | 29/08/2023 | Aberystwyth Town | - | Pontypridd United | 0:1 | ||||
| 5. Round | 02/09/2023 | Pontypridd United | - | Barry Town United | 1:0 | ||||
| 7. Round | 16/09/2023 | Pontypridd United | - | Bala Town | 0:0 | ||||
| 8. Round | 23/09/2023 | Caernarfon Town | - | Pontypridd United | 1:0 | ||||
| 9. Round | 26/09/2023 | Pontypridd United | - | Newtown AFC | 0:1 | ||||
| 11. Round | 07/10/2023 | Pontypridd United | - | Haverfordwest County | 2:0 | ||||
| 12. Round | 17/10/2023 | Barry Town United | - | Pontypridd United | 2:0 | ||||
| 13. Round | 21/10/2023 | Pontypridd United | - | Connah's Quay Nomads | 0:3 |  |
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| 14. Round | 28/10/2023 | Pontypridd United | - | Cardiff Metropolitan | 1:3 | ||||
| 17. Round | 28/11/2023 | Newtown AFC | - | Pontypridd United | 3:1 | ||||
| 18. Round | 02/12/2023 | Pontypridd United | - | Caernarfon Town | 1:2 | ||||
| 19. Round | 16/12/2023 | Connah's Quay Nomads | - | Pontypridd United | 3:1 |
Wales
Barbados