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.| Tie no | Home | Score | Away |
| 1 | Chester | 1–4 | Rhyl |
Semifinal
Bangor City and Lovell's Athletic played at Wrexham, replay at Newtown; Cardiff City and Wrexham played at Shrewsbury.| Tie no | Home | Score | Away |
| 1 | Bangor City | 0–0 | Lovell's Athletic |
| replay | Bangor City | ||
| 2 | Cardiff City | 6–0 | Wrexham |
Final
Final were held at Newport.| Tie no | Home | Score | Away |
| 1 | Cardiff City | 2–0 | Lovell's Athletic |