1958–59 Welsh Cup

The 1958–59 FAW Welsh Cup is the 72nd season of the annual knockout tournament for competitive football teams in Wales.

Key
League name pointed after clubs name.
 * B&DL - Birmingham & District League
 * FL D2 - Football League Second Division
 * FL D3 - Football League Third Division
 * FL D4 - Football League Fourth Division
 * SFL - Southern Football League

Fifth round
Ten winners from the Fourth round and six new clubs.

Semifinal
Bangor City and Lovell's Athletic played at Wrexham, replay at Newtown; Cardiff City and Wrexham played at Shrewsbury.

Final
Final were held at Newport.