The 1958–59 season was Port Vale's 48th season of football in the Football League, and their first season in the Third Division following their promotion from the Fourth Division. Progressing to the Fifth Round of the FA Cup, there they set a Vale Park and club-record attendance of 49,768, in a 2–1 defeat by Aston Villa on 20 February. In the first of a short-lived Supporters' Clubs' Trophy, they lost to rivals Stoke City 5–3 on aggregate; whilst in the league they finished a respectable fourteenth, thirteen points from both promotion and relegation.

The pre-season saw the arrival of Morgan Hunt from Norwich City for a four-figure fee, and outside-left Cliff Portwood from Preston North End for £750.

The season began with a 3–2 win over Reading at Elm Park, Norman Low having selected a first eleven without any of the new signings. However, after a 1–0 win over Bournemouth & Boscombe Athletic Vale began to struggle, picking up just a point in their next six games. Low tried to sign Stanley Matthews, still going strong aged 44 for Blackpool, but a deal could not be reached. On 5 September, Tranmere Rovers beat Vale 6–0 at Prenton Park after Roy Sproson left the field in the first half with a gashed leg. Low then traded John Cunliffe and £2,000 to Stoke City in exchange for winger Harry Oscroft and centre-half Peter Ford. An improvement took place, and despite trouble in front of goal, the team won seven successive games at Burslem. In October, Jack Wilkinson was sold to Exeter City for £2,500, having lost his place in the starting eleven. On 28 December, Vale recorded a 7–0 win over Halifax Town, causing The Sentinel's "T.G.F." to remark that "rarely have the opposition been so completely outplayed".

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