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| 21.07.2023 | 19:30 | Baglan Dragons | - | Afan Lido FC | 1:3 (0:1) | |
| 19:45 | Chirk AAA | - | Denbigh Town | 0:1 (0:1) | ||
| 20:30 | Cambrian & Clydach | - | Cardiff City U23 | 3:4 (1:2) pn. | ||
| 20:30 | Llanelli Town | - | Pontardawe Town | 1:0 (0:0) | ||
| 20:30 | Abergavenny Town | - | Briton Ferry Llansawel AFC | 0:2 (0:2) | ||
| 20:30 | Ruthin Town | - | Llandudno FC | 3:2 (1:2) | ||
| 22.07.2023 | 15:30 | Goytre United | - | Llantwit Major FC | 1:2 (1:1) | |
| 15:30 | Cwmbran Celtic | - | Taff's Well AFC | 0:3 (0:0, 2:2) pn. | ||
| 15:30 | Carmarthen Town | - | Swansea City Sub-21 | 0:4 | ||
| 15:30 | Caersws FC | - | Guilsfield FC | 1:3 (1:0) | ||
| 15:30 | Holywell Town | - | Bangor 1876 FC | 2:3 (1:0) | ||
| 15:30 | Porthmadog FC | - | Llanidloes Town FC | 4:2 (0:1) | ||
| 15:30 | Buckley Town | - | Mold Alexandra | 2:1 (1:0) | ||
| 25.07.2023 | 20:45 | Abertillery Bluebirds | - | Ammanford AFC | 0:2 (0:0) |
