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.

Third round
8 winners from the Second round, Caerphilly United and Llanerch Celts plus 16 new clubs.

Fourth round
12 winners from the Third round. Lovell's Athletic get a bye to the Fifth round.

Fifth round
Six winners from the Fourth round, Lovell's Athletic plus nine new clubs.

Sixth round
Eight winners from the Fifth round plus Chester and Newport County.

Seventh round
Two winners from the Sixth round. Cardiff City, South Liverpool and Chester get a bye to the Semifinals.

Semifinal
South Liverpool and Chester played at Goodison Park, the second replay between Cardiff City and Oswestry Town were held at Shrewsbury.

Final
Final were held at Wrexham.