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| 19/09/2023 | 19:30 | Buckley Town | - | Gresford Athletic | 0:1 (0:1) | |
| 19:30 | Afan Lido FC | - | Cardiff Metropolitan | 0:4 (0:1) | ||
| 19:30 | Ammanford AFC | - | Briton Ferry Llansawel AFC | 0:1 (0:1) | ||
| 19:30 | Swansea City U23 | - | Cardiff City U23 | 5:3 (1:0, 1:1) pso | ||
| 19:45 | The New Saints | - | Porthmadog FC | 4:1 (2:1) | ||
| 19:45 | Guilsfield FC | - | Bala Town | 1:0 (0:0) | ||
| 20:00 | Aberystwyth Town | - | Pontypridd United | 0:1 (0:0) | ||
| 03/10/2023 | 19:45 | Prestatyn Town | - | Colwyn Bay FC | 4:1 (0:2, 2:2) pso |
