May began his career with Scottish junior side Thorniewood United before signing for Cardiff City in 1948.
Although he played as a full back, he made his professional debut as a forward during an injury crisis in a 1–0 defeat to Leicester City.
[2] At Swindon, he was able to establish himself in the first team and made 78 league appearances during a two-year spell before moving to Barnsley.
[3] May was ever present for Barnsley as they won the Third Division North title during the 1954–55 season, playing in every league match.
However, a dispute over wages eventually led him to leave the club in 1955, finishing his professional career with Southend United.