1957–58 Welsh Cup
| Tournament details | |
|---|---|
| Country | Wales | 
| Final positions | |
| Champions | |
| Runners-up | |
The 1957–58 FAW Welsh Cup is the 71st 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 D3N - Football League Third Division North
 - FL D3S - Football League Third Division South
 - SFL - Southern Football League
 
Fifth round
Ten winners from the Fourth round and six new clubs.
| Tie no | Home | Score | Away | 
|---|---|---|---|
| 1 | Oswestry Town (B&DL) | 1–3 | Chester (FL D3N) | 
Sixth round
| Tie no | Home | Score | Away | 
|---|---|---|---|
| 1 | Chester (FL D3N) | 2–0 | Swansea Town (FL D2) | 
Semifinal
Chester and Hereford United played at Wrexham, replay - at Swansea, Caernarfon Town and Wrexham played at Bangor.
| Tie no | Home | Score | Away | 
|---|---|---|---|
| 1 | Chester (FL D3N) | 1–1 | Hereford United (SFL) | 
| replay | Chester (FL D3N) | 2–0 | Hereford United (SFL) | 
| 2 | Caernarfon Town (WLN) | 2–4 | Wrexham (FL D3N) | 
Final
Final were held at Chester, replay - at Wrexham.
| Tie no | Home | Score | Away | 
|---|---|---|---|
| 1 | Chester (FL D3N) | 1–1 | Wrexham (FL D3N) | 
| replay | Wrexham (FL D3N) | 2–1 | Chester (FL D3N) |