1938–39 Welsh Cup
The 1938–39 FAW Welsh Cup is the 58th season of the annual knockout tournament for competitive football teams in Wales.Key
League name pointed after clubs name.
Second round
14 winners from the First round plus Llay United and Rhayader. Caerphilly United and Llanerch Celts get a bye to the Third round.
| Tie no | Home | Score | Away |
| 1 | Porthmadog | 3–4 | Llandudno |
| 2 | Flint Athletic | 1–1 | Shotton Athletic |
| replay | Shotton Athletic | 5–2 | Flint Athletic |
| 3 | Blaenau Ffestiniog | 4–1 | Caernarfon Town |
| 4 | Machynlleth | 4–0 | Aberdovey |
| 5 | Llanidloes Town | 3–0 | Aberystwyth Town |
| 6 | Druids | 0–3 | Cross Street Gwersyllt |
| 7 | Rhayader | 1–2 | Welshpool |
| 8 | Llay United | 2–0 | Buckley Town |
Third round
8 winners from the Second round, Caerphilly United and Llanerch Celts plus 16 new clubs.
| Tie no | Home | Score | Away |
| 1 | Shotton Athletic | 3–1 | Blaenau Ffestiniog |
| 2 | Llay United | 0–4 | Llanidloes Town |
| 3 | Llanerch Celts | 4–2 | Machynlleth |
| 4 | Oswestry Town | 3–2 | Llandudno |
| 5 | Cross Street Gwersyllt | 2–1 | Welshpool |
| 6 | Hereford United | w/o | Kidderminster Harriers |
| 7 | Caerphilly United | 2–4 | Troedyrhiw |
| 8 | Aberdare Town | 2–6 | Aberaman |
| 9 | Haverfordwest Athletic | 2–1 | Llanelly |
| 10 | Barry | 7–1 | Cardiff Corinthians |
| 11 | Caerau Athletic | 1–4 | Gwynfi Welfare |
| 12 | Milford United | 10–2 | Caerphilly Town |
| 13 | Ebbw Vale | 2–2 | Lovell's Athletic |
| replay | Lovell's Athletic | 4–1 | Ebbw Vale |
Fourth round
12 winners from the Third round. Lovell's Athletic get a bye to the Fifth round.
| Tie no | Home | Score | Away |
| 1 | Oswestry Town | 5–1 | Hereford United |
| 2 | Shotton Athletic | 4–1 | Cross Street Gwersyllt |
| 3 | Llanidloes Town | 5–0 | Llanerch Celts |
| 4 | Haverfordwest Athletic | 3–2 | Gwynfi Welfare |
| 5 | Barry | w/o | Aberaman |
| 6 | Milford United | 8–2 | Troedyrhiw |
Fifth round
Six winners from the Fourth round, Lovell's Athletic plus nine new clubs.
| Tie no | Home | Score | Away |
| 1 | Wrexham | 9–0 | Southport |
| 2 | Bangor City | 0–1* | New Brighton |
| replay | Bangor City | 2–0 | New Brighton |
| 3 | Cardiff City | 2–2 | Swansea Town |
| replay | Swansea Town | 1–4 | Cardiff City |
| 4 | Rhyl | 3–0 | Shotton Athletic |
| 5 | Oswestry Town | 2–0 | Llanidloes Town |
| 6 | South Liverpool | 2–1 | Shrewsbury Town |
| 7 | Haverfordwest Athletic | 2–3 | Milford United |
| 8 | Barry | 2–0 | Lovell's Athletic |
Sixth round
Eight winners from the Fifth round plus Chester and Newport County.
| Tie no | Home | Score | Away |
| 1 | Chester | 4–0 | Rhyl |
| 2 | Cardiff City | 5–1 | Newport County |
| 3 | South Liverpool | 8–1 | Bangor City |
| 4 | Barry | 1–0 | Wrexham |
| 5 | Milford United | 2–2 | Oswestry Town |
| replay | Oswestry Town | 4–0 | Milford United |
Seventh round
Two winners from the Sixth round. Cardiff City, South Liverpool and Chester get a bye to the Semifinals.
| Tie no | Home | Score | Away |
| 1 | Oswestry Town | 4–2 | Barry |
Semifinal
South Liverpool and Chester played at Goodison Park, the second replay between Cardiff City and Oswestry Town were held at Shrewsbury.
| Tie no | Home | Score | Away |
| 1 | South Liverpool | 5–2 | Chester |
| 2 | Cardiff City | 1–1 | Oswestry Town |
| replay | Oswestry Town | 2–2 | Cardiff City |
| replay | Cardiff City | 2–1 | Oswestry Town |
Final
Final were held at Wrexham.
| Tie no | Home | Score | Away |
| 1 | South Liverpool | 2–1 | Cardiff City |
