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1/64-finals
1/32-finals
1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2008/09
1/64-finals
| 1 | Aberystwyth | Bye | |
| 2 | Cwmamman United | Afan Lido | 0 : 3 |
| 3 | Newport Civil Service | Grange Harlequins | 5 : 1 |
| 4 | Bye | Caersws FC | |
| 5 | Flint | Rhos Aelwyd | 4 : 3 |
| 6 | Brymbo | Mold Alexandra | 0 : 8 |
| 7 | Llanwern | Ton Pentre | 3 : 0 |
| 8 | Porthcawl Town | Llwydcoed | 0 : 3 |
| 9 | Goytre Utd | Caerleon | 4 : 1 |
| 10 | Bettws FC | Taffs Well | 1 : 2 |
| 11 | Bryntirion | Treharris Athletic | 9 : 1 |
| 12 | Ely Rangers | Cardiff Corries | 0 : 3 |
| 13 | Gresford | Tredegar Town | 1 : 0 |
| 14 | Cefn United | Rhydymwyn | 0 : 3 |
| 15 | Bala | Glantraeth FC | 6 : 1 |
| 16 | Bye | Prestatyn | |
| 17 | Port Talbot | Bye | |
| 18 | Barry | Aberaman | 1 : 2 |
| 19 | Chirk AAA FC | Nantlle Vale FC | 3 : 0 |
| 20 | Llanllyfni | Denbigh | 1 : 4 |
| 21 | Tywyn Bryncrug | Bethesda Athletic | 4 : 1 |
| 22 | Berriew FC | Llangollen | 0 : 1 |
| 23 | Neath Athletic | Bye | |
| 24 | Bye | Llanelli | |
| 25 | TNS | Bye | |
| 26 | Ruthin | Guilsfield | 0 : 2 |
| 27 | Maesteg Park | Croesyceiliog | 3 : 0 |
| 28 | Conwy Borough | Penrhyncoch | 2 : 3 |
| 29 | Pwllheli | Llanrug | 2 : 0 |
| 30 | Penparcau FC | Llandudno Junction | 2 : 4 |
| 31 | Bow Street | Llanberis | 3 : 2 |
| 32 | Bye | Carmarthen Town | |
| 33 | Bridgend Town | Pontyclun | 1 : 0 |
| 34 | Cardiff Metropolitan | Cwmbran Town | 1 : 3 |
| 35 | Llanfairpwll FC | Hawarden Rangers | 2 : 0 |
| 36 | Llandudno | Llangefni | 1 : 3 |
| 37 | Porthmadog | Bye | |
| 38 | Bye | Caernarfon | |
| 39 | Glan Conwy | Llanrwst United | 2 : 1 |
| 40 | Venture | Lex XI | 1 : 2 |
| 41 | Holyhead | Mynydd Isa | 4 : 3 |
| 42 | Amlwch Town | Llay Welfare | 1 : 8 |
| 43 | Ammanford | Caldicot | 1 : 0 |
| 44 | Caerau Ely | Pentwyn Dynamo | 1 : 2 |
| 45 | Briton Ferry | Porth | 3 : 1 |
| 46 | Llangeinor | Dinas Powys | 0 : 2 |
| 47 | Cwmbran Celtic | Garw SBGC | 3 : 1 |
| 48 | Cwmaman Institute | Newport YMCA | 2 : 3 |
| 49 | Airbus | Bye | |
| 50 | Bye | Welshpool | |
| 51 | Brickfield | Nefyn United | 4 : 3 |
| 52 | Penycae | Buckley | 3 : 6 |
| 53 | Newtown | Bye | |
| 54 | Newcastle Emlyn | Cambrian & Clydach | 1 : 4 |
| 55 | Halkyn | Coedpoeth | 4 : 2 |
| 56 | Bye | Druids | |
| 57 | Rhyl | Bye | |
| 58 | Llandyrnog United | Castell Alun Colts | 0 : 1 |
| 59 | Pontypridd | Penrhiwceiber Rangers | 4 : 3 |
| 60 | Bye | Haverfordwest | |
| 61 | Garden Village | West End | 3 : 2 |
| 62 | Pontardawe | Risca | 0 : 2 |
| 63 | Connahs Q. | Bye | |
| 64 | Bye | Bangor City |
1/32-finals
| 1 | Aberystwyth | Afan Lido | 3 : 2 |
| 2 | Newport Civil Service | Caersws FC | 0 : 1 |
| 3 | Flint | Mold Alexandra | 4 : 0 |
| 4 | Llanwern | Llwydcoed | 1 : 6 |
| 5 | Goytre Utd | Taffs Well | 2 : 0 |
| 6 | Bryntirion | Cardiff Corries | 1 : 2 |
| 7 | Gresford | Rhydymwyn | 4 : 1 |
| 8 | Bala | Prestatyn | 3 : 4 |
| 9 | Port Talbot | Aberaman | 1 : 0 |
| 10 | Chirk AAA FC | Denbigh | 1 : 4 |
| 11 | Tywyn Bryncrug | Llangollen | 2 : 1 |
| 12 | Neath Athletic | Llanelli | 0 : 4 |
| 13 | TNS | Guilsfield | 4 : 2 |
| 14 | Maesteg Park | Penrhyncoch | 2 : 3 |
| 15 | Pwllheli | Llandudno Junction | 2 : 0 |
| 16 | Bow Street | Carmarthen Town | 1 : 6 |
| 17 | Bridgend Town | Cwmbran Town | 3 : 1 |
| 18 | Llanfairpwll FC | Llangefni | 0 : 3 |
| 19 | Porthmadog | Caernarfon | 5 : 3 |
| 20 | Glan Conwy | Lex XI | 1 : 2 |
| 21 | Holyhead | Llay Welfare | 2 : 1 |
| 22 | Ammanford | Pentwyn Dynamo | 0 : 1 |
| 23 | Briton Ferry | Dinas Powys | 1 : 0 |
| 24 | Cwmbran Celtic | Newport YMCA | 2 : 3 |
| 25 | Airbus | Welshpool | 2 : 1 |
| 26 | Brickfield | Buckley | 3 : 4 |
| 27 | Newtown | Cambrian & Clydach | 1 : 0 |
| 28 | Halkyn | Druids | 2 : 4 |
| 29 | Rhyl | Castell Alun Colts | 8 : 0 |
| 30 | Pontypridd | Haverfordwest | 1 : 4 |
| 31 | Garden Village | Risca | 2 : 0 |
| 32 | Connahs Q. | Bangor City | 0 : 1 |
1/16-finals
| 1 | Aberystwyth | Caersws FC | 3 : 0 |
| 2 | Flint | Llwydcoed | 0 : 1 |
| 3 | Goytre Utd | Cardiff Corries | 6 : 0 |
| 4 | Gresford | Prestatyn | 2 : 3 |
| 5 | Port Talbot | Denbigh | 7 : 0 |
| 6 | Tywyn Bryncrug | Llanelli | 0 : 3 |
| 7 | TNS | Penrhyncoch | 7 : 1 |
| 8 | Pwllheli | Carmarthen Town | 0 : 6 |
| 9 | Bridgend Town | Llangefni | 1 : 0 |
| 10 | Porthmadog | Lex XI | 0 : 2 |
| 11 | Holyhead | Pentwyn Dynamo | 2 : 1 |
| 12 | Briton Ferry | Newport YMCA | 0 : 1 |
| 13 | Airbus | Buckley | 5 : 1 |
| 14 | Newtown | Druids | 0 : 1 |
| 15 | Rhyl | Haverfordwest | 4 : 0 |
| 16 | Garden Village | Bangor City | 0 : 4 |
1/8-finals
| 1 | Aberystwyth | Llwydcoed | 3 : 0 |
| 2 | Goytre Utd | Prestatyn | 3 : 5 |
| 3 | Port Talbot | Llanelli | 2 : 1 |
| 4 | TNS | Carmarthen Town | 2 : 3 |
| 5 | Bridgend Town | Lex XI | 4 : 0 |
| 6 | Holyhead | Newport YMCA | 1 : 2 |
| 7 | Airbus | Druids | 2 : 1 |
| 8 | Rhyl | Bangor City | 1 : 2 |
Quarter-finals
| 1 | Aberystwyth | Prestatyn | 5 : 1 |
| 2 | Port Talbot | Carmarthen Town | 1 : 2 |
| 3 | Bridgend Town | Newport YMCA | 1 : 0 |
| 4 | Airbus | Bangor City | 0 : 5 |
Semi-finals
| 1 | Aberystwyth | Carmarthen Town | 3 : 2 |
| 2 | Bridgend Town | Bangor City | 1 : 2 |
Final
| 1 | Aberystwyth | Bangor City | 0 : 2 |
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