The 1938/39 season was the 66th season of competitive football in Scotland and the 49th season of the Scottish Football League.

Due to the World War II the league was not officially competed for again until the 1946/47 season.

Ayr United continued their improvement under manager Frank Thompson after returning to the First Division with a 14th place finish thanking home wins like the 6-1 victory over Motherwell and 4-1 against Arbroath a for this higher placing.

A friendly match against English club Barnsley was played in April as a benefit match for John Taylor.