1957–58 Welsh Cup
Football tournament season
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Key
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) |
