Group 1
19/08/2008 19:30 Haverfordwest County - Carmarthen Town 1:2
09/09/2008 19:30 Carmarthen Town - Aberystwyth Town 1:1
16/09/2008 19:30 Aberystwyth Town - Haverfordwest County 4:0
23/09/2008 19:30 Carmarthen Town - Haverfordwest County 0:1
07/10/2008 19:30 Haverfordwest County - Aberystwyth Town 1:1
14/10/2008 19:30 Aberystwyth Town - Carmarthen Town 1:1
Group 2
19/08/2008 19:30 Llanelli AFC - Neath FC 3:5
02/09/2008 19:30 Port Talbot Town - Llanelli AFC 1:4
09/09/2008 19:30 Neath FC - Port Talbot Town 5:3
24/09/2008 19:30 Neath FC - Llanelli AFC 0:3
07/10/2008 19:30 Llanelli AFC - Port Talbot Town 2:4
14/10/2008 19:30 Port Talbot Town - Neath FC 3:3
Group 3
19/08/2008 19:30 Newtown AFC - Caernarfon Town 7:1
02/09/2008 19:30 NEWI Cefn Druids - Newtown AFC 0:2
09/09/2008 19:30 Caernarfon Town - NEWI Cefn Druids 1:1
24/09/2008 19:30 Caernarfon Town - Newtown AFC 0:0
07/10/2008 19:30 Newtown AFC - NEWI Cefn Druids 2:3
14/10/2008 19:30 NEWI Cefn Druids - Caernarfon Town 3:2
Group 4
19/08/2008 19:30 Porthmadog FC - Caersws FC 2:3
02/09/2008 19:30 Bangor City - Porthmadog FC 3:0
09/09/2008 19:30 Caersws FC - Bangor City 3:3
23/09/2008 19:30 Caersws FC - Porthmadog FC 1:1
07/10/2008 19:30 Porthmadog FC - Bangor City 2:3
21/10/2008 19:30 Bangor City - Caersws FC 1:6
Group 5
19/08/2008 19:30 Rhyl FC - Airbus UK 6:1
02/09/2008 19:30 Rhyl FC - Technogroup Welshpool Town 1:2
09/09/2008 19:30 Airbus UK - Technogroup Welshpool Town 2:0
23/09/2008 19:30 Airbus UK - Rhyl FC 0:4
07/10/2008 19:30 Technogroup Welshpool Town - Rhyl FC 0:2
14/10/2008 19:30 Technogroup Welshpool Town - Airbus UK 5:2
Group 6
19/08/2008 19:30 GAP Connah's Quay FC - The New Saints 0:2
02/09/2008 19:30 Prestatyn Town - GAP Connah's Quay FC 0:1
09/09/2008 19:30 The New Saints - Prestatyn Town 3:3
23/09/2008 19:30 The New Saints - GAP Connah's Quay FC 3:0
07/10/2008 19:30 GAP Connah's Quay FC - Prestatyn Town 2:1
14/10/2008 19:30 Prestatyn Town - The New Saints 3:4
Quarter-finals
28/10/2008 19:30 Bangor City - Rhyl FC 3:1 aet
04/11/2008 19:30 NEWI Cefn Druids - The New Saints 0:2
19:30 Newtown AFC - Neath FC 2:4 pso
25/11/2008 19:30 Aberystwyth Town - Caersws FC 4:1
Semi-finals
25/11/2008 19:30 Neath FC - The New Saints 2:0
09/12/2008 19:30 Bangor City - Aberystwyth Town 1:2
19:30 The New Saints - Neath FC 3:0
13/01/2009 19:30 Aberystwyth Town - Bangor City 2:4
Final
05/04/2009 13:00 Bangor City - The New Saints 0:2