In the 1937–38 English football season, Gillingham F.C. competed in the Football League Third Division South, the third tier of the English football league system. It was the eighteenth season in which Gillingham competed in the Football League. The team won only three times in nineteen Football League matches between August and December; in November and December, they played six league games and lost each one without scoring a goal, leaving them at the bottom of the division at the end of 1937. Although Gillingham's performances improved in the second half of the season, with seven wins between January and May, they remained in last place at the end of the season, meaning that the club was required to apply for re-election to the League. The application was rejected, and as a result the club lost its place in the Football League and joined the regional Southern League. The team were eliminated in the first round of the FA Cup but reached the second round of the Third Division South Cup.
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