Grupo 1
19.08.2008 20:30 Haverfordwest County - Carmarthen Town 1:2
09.09.2008 20:30 Carmarthen Town - Aberystwyth Town 1:1
16.09.2008 20:30 Aberystwyth Town - Haverfordwest County 4:0
23.09.2008 20:30 Carmarthen Town - Haverfordwest County 0:1
07.10.2008 20:30 Haverfordwest County - Aberystwyth Town 1:1
14.10.2008 20:30 Aberystwyth Town - Carmarthen Town 1:1
Grupo 2
19.08.2008 20:30 Llanelli AFC - Neath FC 3:5
02.09.2008 20:30 Port Talbot Town - Llanelli AFC 1:4
09.09.2008 20:30 Neath FC - Port Talbot Town 5:3
24.09.2008 20:30 Neath FC - Llanelli AFC 0:3
07.10.2008 20:30 Llanelli AFC - Port Talbot Town 2:4
14.10.2008 20:30 Port Talbot Town - Neath FC 3:3
Grupo 3
19.08.2008 20:30 Newtown AFC - Caernarfon Town 7:1
02.09.2008 20:30 NEWI Cefn Druids - Newtown AFC 0:2
09.09.2008 20:30 Caernarfon Town - NEWI Cefn Druids 1:1
24.09.2008 20:30 Caernarfon Town - Newtown AFC 0:0
07.10.2008 20:30 Newtown AFC - NEWI Cefn Druids 2:3
14.10.2008 20:30 NEWI Cefn Druids - Caernarfon Town 3:2
Grupo 4
19.08.2008 20:30 Porthmadog FC - Caersws FC 2:3
02.09.2008 20:30 Bangor City - Porthmadog FC 3:0
09.09.2008 20:30 Caersws FC - Bangor City 3:3
23.09.2008 20:30 Caersws FC - Porthmadog FC 1:1
07.10.2008 20:30 Porthmadog FC - Bangor City 2:3
21.10.2008 20:30 Bangor City - Caersws FC 1:6
Grupo 5
19.08.2008 20:30 Rhyl FC - Airbus UK 6:1
02.09.2008 20:30 Rhyl FC - Technogroup Welshpool Town 1:2
09.09.2008 20:30 Airbus UK - Technogroup Welshpool Town 2:0
23.09.2008 20:30 Airbus UK - Rhyl FC 0:4
07.10.2008 20:30 Technogroup Welshpool Town - Rhyl FC 0:2
14.10.2008 20:30 Technogroup Welshpool Town - Airbus UK 5:2
Grupo 6
19.08.2008 20:30 GAP Connah's Quay FC - The New Saints 0:2
02.09.2008 20:30 Prestatyn Town - GAP Connah's Quay FC 0:1
09.09.2008 20:30 The New Saints - Prestatyn Town 3:3
23.09.2008 20:30 The New Saints - GAP Connah's Quay FC 3:0
07.10.2008 20:30 GAP Connah's Quay FC - Prestatyn Town 2:1
14.10.2008 20:30 Prestatyn Town - The New Saints 3:4
Cuartos de final
28.10.2008 20:30 Bangor City - Rhyl FC 3:1 pró.
04.11.2008 20:30 NEWI Cefn Druids - The New Saints 0:2
20:30 Newtown AFC - Neath FC 2:4 pn.
25.11.2008 20:30 Aberystwyth Town - Caersws FC 4:1
Semifinales
25.11.2008 20:30 Neath FC - The New Saints 2:0
09.12.2008 20:30 Bangor City - Aberystwyth Town 1:2
20:30 The New Saints - Neath FC 3:0
13.01.2009 20:30 Aberystwyth Town - Bangor City 2:4
Final
05.04.2009 14:00 Bangor City - The New Saints 0:2
League Cup
League Cup