Forward Fred Cheesmur scored six goals in a match against Merthyr Town on 26 April 1930, a club record haul for a single match at a professional level which stands to this day.[2]
Gillingham's first match of the season was at home to Walsall at Priestfield Road. New signings Smith, Beacham, Collins, Bishop, McCafferty, Cheesmur and Castle all made their debuts. Castle and Cheesmur scored the goals in a 2–1 victory for Gillingham. The attendance of 8,160 would prove to be the largest crowd of the season at Priestfield Road.[3]
January–May
In the penultimate game of the season, Gillingham beat Merthyr Town 6–0; Cheesmur scored all the goals. It was the first time a Gillingham player had scored as many goals in a single game at a professional level and a record that stands to this day. The final match of the season was at home to Luton Town; Cheesmur and John Speed scored in a 2–0 win. Gillingham had ended the season with an unbeaten run of six games, comprising four wins and two draws, but still finished 21st in the division, ahead of only Merthyr Town.
Gillingham entered the 1929–30 FA Cup in the first round, and were paired with Margate of the Kent League, who had progressed from the qualifying rounds for the first time. In what was seen as a significant upset, Gillingham lost 2–0 to their lower-level opponents and were eliminated from the competition.[10]
Twenty-seven players made at least one appearance for Gillingham during the season. George Bishop and Fred Cheesmur made the most, each playing in 41 of the team's 43 competitive matches; four other players each played more than 30 times. Ronald Baird was the only player to make just one appearance; he played against Coventry City in March, but it would prove to be the only game of his professional career.
Thirteen players scored at least one goal for Gillingham during the season. Cheesmur was the top goalscorer with 17 goals; no other player reached double figures.
As a result of finishing 21st, Gillingham were required to apply for re-election for the second consecutive season, but were again re-elected. In the following season, the team finished 16th in the Third Division South.