| 1. Round | 11/08/2023 | Haverfordwest County | - | Pontypridd United | 0:0 | ||||
| 2. Round | 19/08/2023 | Pontypridd United | - | The New Saints | 0:1 | ||||
| 3. Round | 25/08/2023 | Pontypridd United | - | Penybont FC | 0:0 | ||||
| 4. Round | 29/08/2023 | Aberystwyth Town | - | Pontypridd United | 0:1 | ||||
| 6. Round | 08/09/2023 | Cardiff Metropolitan | - | Pontypridd United | 2:0 |  |
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| 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 | ||||
| 10. Round | 30/09/2023 | The New Saints | - | Pontypridd United | 4:0 | ||||
| 11. Round | 07/10/2023 | Pontypridd United | - | Haverfordwest County | 2:0 | ||||
| 12. Round | 17/10/2023 | Barry Town United | - | Pontypridd United | 2:0 | ||||
| 15. Round | 04/11/2023 | Bala Town | - | Pontypridd United | 0:0 | ||||
| 20. Round | 26/12/2023 | Pontypridd United | - | Aberystwyth Town | 2:0 | ||||
| 21. Round | 31/12/2023 | Penybont FC | - | Pontypridd United | 1:0 | ||||
| 22. Round | 13/01/2024 | Colwyn Bay FC | - | Pontypridd United | 2:3 |
Wales