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.

In Gillingham's 17 seasons in this division, the team had consistently struggled, only finishing in the top half of the league table three times.

[2][3] Alan Ure was the club's manager; he had been appointed at the conclusion of the previous season following the resignation of Fred Maven.

[5] The club signed several players ahead of the new season, including half-back Jimmy Nichol, who arrived from Portsmouth.

Nichol had spent three seasons with Gillingham in the 1920s and returned for a second spell with the club at the age of 34;[6][7] he was appointed team captain.

[13][14] Four days later, Gillingham played the first game of the season at their home ground, Priestfield Road; a goal from Walker gave them a 1–0 win over Newport County.

The Daily Herald's reporter praised Gillingham's full-backs and forwards but identified the poor quality of their half-backs as a "serious problem".

[13] The run of defeats ended with a 5–3 victory away to Exeter City on 18 September, the most goals the team would score in a match during the season.

Full-back George Tweed, a new signing from Bristol Rovers, made his debut on 23 October and would play in every game for the remainder of the season.

A week later, Gillingham lost again, being defeated 5–1 at home by Queens Park Rangers, the first time they had conceded as many goals during the season.

[13] The team remained unbeaten for the remainder of the month with two draws and a victory over Exeter City[13] but stayed bottom of the table.

Gillingham finished the game with ten men after Frank Donoghue, making his Football League debut, was carried off injured.

The sequence began with a 3–0 defeat away to Crystal Palace; Norman Brickenden, a 23-year old goalkeeper, made his debut and was praised for his performance by the correspondent for the Daily News, but the same writer criticised Gillingham's forwards as "unbalanced" and "too individualistic" in their play.

[34][35] After beating Southend United the next day Gillingham lost again to Crystal Palace, taking a 2–0 lead in the first half before conceding four goals after the interval.

Several fringe players were brought into the team in place of regular starters, and Gillingham lost 4–0, ending their participation in the competition.

He was the only player to reach double figures; Herbert had the second-highest total, despite playing in fewer than half the team's games, with seven goals.

[13] FW = Forward, HB = Half-back, GK = Goalkeeper, FB = Full-back As a result of finishing last, Gillingham were again required to apply for re-election.