(Source: AllWalesSport)
(Image: Colin Ewart)
| October 2019 | |||
| Round 1 | |||
| Afan Lido | 7 | 0 | Caldicot Town |
| Brickfield Rangers | 1 | 4 | Mynydd Isa |
| Briton Ferry Llansawel | 2 | 0 | Canton Liberal |
| Caernarfon Town | 2 | 0 | Colwyn Bay |
| Cambrian & Clydach | 1 | 1 | Ton Pentre |
| Ton Pentre won 5-3 on pens. | |||
| Cardiff Draconians | 6 | 0 | Haverfordwest County |
| Chirk AAA | 6 | 0 | Lex XI |
| Flint Town Utd | 4 | 1 | Prestatyn Town |
| Goytre United | 2 | 6 | Risca United |
| Llanelli Town | 10 | 1 | Port Talbot Town |
| Llangefni Town | 1 | 3 | Bala Town |
| Llanidloes | 2 | 1 | Welshpool Town |
| Newport County | 1 | 7 | Trefelin BGC |
| Newtown | 3 | 2 | Bow Street |
| Porthmadog | 6 | 3 | Penmaenmawr Phoenix |
| Rhydymwyn | 2 | 4 | Llandudno |
| Taffs Well | 2 | 2 | Carmarthen Town |
| Taffs Well won 5-4 on pens. | |||
| Wrexham | 16 | 1 | Buckley Town |
| 13 October 2019 | |||
| Round 1 | |||
| Newcastle Emlyn | 4 | 2 | Llanfair United |
| 19 October 2019 | |||
| Round 1 | |||
| Cefn Cribwr | 2 | 1 | Tredegar Town |
| a.e.t. |
| 3 November 2019 | |||
| Round 2 | |||
| Aberystwyth Town | 1 | 2 | Taffs Well |
| Bala Town | 2 | 3 | Chirk AAA |
| Caernarfon Town | 3 | 1 | Cefn Druids |
| Flint Town Utd | 0 | 5 | Connahs Quay |
| Garden Village | 5 | 5 | Afan Lido |
| Afan Lido won 6-5 on pens. | |||
| Llandudno | 8 | 1 | Llanidloes |
| Newcastle Emlyn | 2 | 6 | Mynydd Isa |
| Penybont | 1 | 2 | Briton Ferry Llansawel |
| Pontardawe Town | 6 | 0 | Llanelli Town |
| Porthmadog | 0 | 5 | Newtown |
| The New Saints | 6 | 1 | Rhyl |
| Ton Pentre | 3 | 1 | Cardiff Draconians |
| Wrexham | 2 | 3 | Airbus UK |
| 10 November 2019 | |||
| Round 2 | |||
| Caerau Ely | 3 | 0 | Cardiff Met |
| Trefelin BGC | 2 | 7 | Risca United |
| 24 November 2019 | |||
| Round 3 | |||
| Airbus UK | 3 | 0 | Connahs Quay |
| Briton Ferry Llansawel | 0 | 5 | Pontardawe Town |
| Caernarfon Town | 1 | 3 | Newtown |
| Chirk AAA | 7 | 0 | Llandudno |
| Mynydd Isa | 2 | 3 | The New Saints |
| Risca United | 2 | 2 | Barry Town United |
| Barry Town United won 4-2 on pens. | |||
| Ton Pentre | 2 | 1 | Afan Lido |
| 1 December 2019 | |||
| Round 3 | |||
| Caerau Ely | 3 | 1 | Taffs Well |
| a.e.t. |
| Quarter Final | |||
| Barry Town United | 3 | 1 | Airbus UK |
| Chirk AAA | 1 | 0 | Pontardawe Town |
| Newtown | 3 | 1 | Ton Pentre |
| The New Saints | 5 | 3 | Caerau Ely |
