Primera etapa
02.08.2019 20:30 Briton Ferry Llansawel AFC - Taff's Well AFC 3:1 (1:0)
03.08.2019 15:30 Buckley Town - Rhyl FC 0:2 (0:1)
15:30 Ruthin Town - Guilsfield FC 0:3 (0:2)
15:30 Prestatyn Town - Llanrhaeadr-ym-Mochnant 4:2 (1:1)
15:30 Llanfair United - Llangefni Town FC 3:1 (1:1)
15:30 Berriew FC - Corwen FC 0:2 (0:0)
15:30 Afan Lido FC - Cwmbran Celtic 0:1 (0:0)
15:30 Pontypridd Town - STM Sports 2:3 (2:2)
15:30 Undy Athletic - Cwmamman United 4:5 (1:0, 2:2) pn.
15:30 Swansea University - Llantwit Major FC 0:1 (0:1)
15:30 Goytre United - Caerau Ely AFC 3:0 (0:0)
15:30 Ammanford AFC - Penrhyncoch FC 2:1 (2:0)
04.08.2019 15:30 Gresford Athletic - Colwyn Bay FC 1:0 (0:0)
04.09.2019 20:30 Conwy Borough FC - Bangor City 0:1 (0:0)
Segunda etapa
09.08.2019 20:45 Bala Town - Gresford Athletic 7:0 (2:0)
20:45 Penybont FC - Goytre United 4:1 (1:1)
10.08.2019 15:30 Corwen FC - Caernarfon Town 0:2 (0:2)
15:30 Rhyl FC - Connah's Quay Nomads 0:2 (0:2)
15:30 Airbus UK - Llanfair United 4:0 (1:0)
15:30 Cefn Druids - Prestatyn Town 1:2 (0:1)
15:30 Flint Town United - Porthmadog FC 5:1 (3:0)
15:30 Guilsfield FC - Llandudno FC 1:0 (0:0)
15:30 Cambrian & Clydach - Aberystwyth Town 3:4 (1:2)
15:30 Haverfordwest County - Barry Town United 4:3 (0:1, 1:1) pn.
15:30 Newtown AFC - Ammanford AFC 2:0 (1:0)
15:30 Carmarthen Town - Cwmamman United 4:1 (1:1)
15:30 Llantwit Major FC - Cardiff Metropolitan 1:2 (0:0)
15:30 Briton Ferry Llansawel AFC - Llanelli Town 3:0 (0:0, 1:1) pn.
15:30 STM Sports - Cwmbran Celtic 4:0 (1:0)
24.09.2019 20:45 Bangor City - The New Saints 4:2 (0:0, 1:1) pn.
Octavos de final
24.09.2019 20:45 Briton Ferry Llansawel AFC - Carmarthen Town 0:2 (0:1)
20:45 Caernarfon Town - Prestatyn Town 1:4 (0:2)
20:45 Cardiff Metropolitan - Aberystwyth Town 0:1 (0:1)
20:45 Flint Town United - Airbus UK 2:1 (1:0)
20:45 Newtown AFC - Penybont FC 2:1 (0:0)
25.09.2019 20:45 Guilsfield FC - Connah's Quay Nomads 3:5 (0:1, 1:1) pn.
01.10.2019 20:30 STM Sports - Haverfordwest County 7:6 pn.
08.10.2019 20:45 Bala Town - Bangor City 7:6 (1:0, 1:1) pn.
Cuartos de final
29.10.2019 20:45 Prestatyn Town - Bala Town 1:2 (1:0)
20:45 Connah's Quay Nomads - Flint Town United 4:1 (1:0)
20:45 Newtown AFC - STM Sports 3:4 (1:1, 2:2) pn.
20:45 Carmarthen Town - Aberystwyth Town 0:3 (0:1)
Semifinales
23.11.2019 15:30 STM Sports - Aberystwyth Town 2:1 (1:1)
15:30 Connah's Quay Nomads - Bala Town 2:0 (2:0)
Final
01.02.2020 18:15 Connah's Quay Nomads - STM Sports 3:0 (2:0)
League Cup
League Cup