The 1938–39 season was Port Vale's 33rd season of football in the Football League, and their first ever season in the Third Division South, having switched from the Third Division North in summer 1938. It was the club's last full season of football before the breakout of war in Europe. It was thus the last season of competitive football for many of the players, including Tom Nolan, who became the club's top scorer for the fourth and final time with seventeen goals. Progressing to the semi-final stage of the Football League Third Division South Cup, they could progress no further as the tournament was cancelled before its conclusion. Manager Tom Morgan shocked the club by leaving for another position in March.

The pre-season saw another reconstruction of the first eleven, as eleven new signings arrived at The Old Recreation Ground, most notably: highly rated goalkeeper Arthur Jepson (Grantham Town); veteran left-back George Collin (Sunderland); right-half George Hannah (Derby County); left-half Sid Wileman (signed from Derby for 'a substantial fee'); and goalscoring winger John Callender (Lincoln City). Work at the stadium took place, as ground outside the stadium was prepared for car parking. The eclectic training schedule of the previous season was expanded, with bowls and cricket supplemented by games of tennis and baseball. Also on 20 August, a Football League Jubilee Fund match was played against nearby Crewe Alexandra, with the Vale picking up a 3–2 win, raising £243 in the process.

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