[5] In July, George Collins was appointed as Gillingham's new manager in place of Sam Gilligan, who did not return to the club after the war.

[7] The new signings included Arthur Wood, a forward who had last played for Fulham of the Football League Second Division; he was able to resume his career despite having suffered an injury while fighting in the war which necessitated the insertion of a metal plate into his forehead and limited his ability to head the ball.

[8] Other new players to join Gillingham included Bobby Beale, a goalkeeper born in nearby Maidstone who had previously played over a hundred Football League games for Manchester United,[9] and David Chalmers, a Scottish forward who had also seen active service during the war.

[16] The run included a 5–0 loss away to Cardiff City, in which the Cardiff-based Western Mail contended that Gillingham's defence, prior to this game one of the best in the league, had experienced a "sensational collapse" and that the home team's goalkeeper was "practically a spectator".

[22][23] Another new forward, H. Kelly, debuted against Norwich, as did half-backs Alex Steel and Jimmy Kennedy, signed from Southend United and Watford respectively.

[16] Gillingham played only two league games in January and their winless run continued as they lost away to Watford and Exeter City.

[16][29] The team lost their next two games, away to Millwall and at home to Brighton & Hove Albion,[30][31] and ended February bottom of the league table, five points below 21st-placed Northampton.

[33] The Chatham Observer praised Abel Lee and the Steel brothers for keeping the Portsmouth forwards in check, and criticised the league leaders for their aggressive style of play.

[36] Gillingham beat Norwich City and Brentford on 10 and 17 April respectively, the first time the team had won two consecutive games since the previous September.

[39] There were further changes to the team for the next game at home to Merthyr Town: half-back Joseph Griffiths made his debut and Len Ramsell played for the first time since January in place of Wood.

Gillingham fell behind to a goal in the first half but scored three times to record their third victory in four games; the Western Mail stated that Merthyr were "very easily beaten".

Gillingham entered the 1919–20 FA Cup at the sixth and final qualifying round stage, where they were paired with fellow Southern League Division One team Swansea Town.

[16][43] The third replay was held at Chelsea's Stamford Bridge stadium; Gillingham took a 2–0 lead in the first half through Bobby Steel and Wood, and finally progressed to the next round, winning the game 3–1; The Daily Telegraph wrote that Gillingham were "the superior side" and that "to beat so decisively the team standing seventh in [the Southern League Division One] was a praiseworthy performance".

In the second half, however, they played poorly and West Stanley scored twice more to win the match and eliminate Gillingham from the competition.

[16] FW = Forward, HB = Half-back, GK = Goalkeeper, FB = Full-back Collins left his position as Gillingham manager at the end of the season and was replaced by Robert Brown.

[50] Initially it was unclear if Gillingham, by virtue of their last-place finish, would be relegated to the Southern League Division Two before this took effect and thus miss out on a place in the Football League; at the club's own AGM on 3 June, angry supporters demanded to know what the club's status would be for the coming season, but the board of directors was unable to give an answer.