| 1958–59 Welsh Cup | |
| Country: | Wales |
| Second: | Lovell's Athletic |
| Prev Season: | 1957–58 |
| Next Season: | 1959–60 |
The 1958–59 FAW Welsh Cup is the 72nd season of the annual knockout tournament for competitive football teams in Wales.
League name pointed after clubs name.
Ten winners from the Fourth round and six new clubs.
| width=50 | Tie no | width=250 | Home | width=50 | Score | width=250 | Away |
|---|---|---|---|---|---|---|---|
| 1 | Chester (FL D4) | 1–4 | Rhyl (CCL) |
Bangor City and Lovell's Athletic played at Wrexham, replay at Newtown; Cardiff City and Wrexham played at Shrewsbury.
| width=50 | Tie no | width=250 | Home | width=50 | Score | width=250 | Away |
|---|---|---|---|---|---|---|---|
| 1 | Bangor City (SFL) | 0–0 | Lovell's Athletic (WLS D1) | ||||
| replay | Bangor City (SFL | 1–2 | Lovell's Athletic (WLS D1) | ||||
| 2 | Cardiff City (FL D2) | 6–0 | Wrexham (FL D3) |
Final were held at Newport.
| width=50 | Tie no | width=250 | Home | width=50 | Score | width=250 | Away |
|---|---|---|---|---|---|---|---|
| 1 | Cardiff City (FL D2) | 2–0 | Lovell's Athletic (WLS D1) |