Last to post wins

[Creeperopolis]

During 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 18th 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 every one without scoring a goal, leaving them 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.

Gillingham also competed in two knock-out competitions. The team were eliminated in the first round of the FA Cup but reached the second round of the Third Division South Cup. The team played 45 competitive matches, winning 11, drawing 6 and losing 28. Jimmy Watson was the club's top goalscorer with 8 goals in Third Division South matches and 13 in all competitions. Dave Whitelaw and Tug Wilson made the most appearances; both played 42 games. The highest attendance recorded at the club's home ground, Priestfield Road, during the season was 9,831 for a game against Millwall on 9 October 1937.