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.- B&DL - Birmingham & District League
- CCL - Cheshire County League
- FL D2 - Football League Second Division
- FL D3N - Football League Third Division North
- FL D3S - Football League Third Division South
- LC - Lancashire Combination
- MWL - Mid-Wales Football League
- ML - Midland League
- SFL - Southern Football League
- WLN - Welsh League North
- WLS D1 - Welsh League South Division One
- WCL - West Cheshire League
- W&DL - Wrexham & District Amateur League
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 |