The highest attendance recorded at the club's home ground, Priestfield Road, was 12,000 for a game against Swindon Town, the eventual Southern League champions.

[5] Prior to the season, Gillingham opted to employ a team manager for the first time since 1908,[6] appointing Sam Gilligan, a forward who had last played for Liverpool, as player-manager.

[9][10][11] The signing of two new forwards followed a season in which no player had scored more than five league goals for Gillingham and the team had finished the campaign as the lowest-scoring side in the division.

[13] Gillingham ended September with a 2–0 defeat away to Brighton & Hove Albion, in which the referee had to warn the players about their conduct after several heated incidents.

[21] The team began October with a second consecutive defeat, losing 1–0 at home to Portsmouth due to a goal scored in the final five minutes of the game,[22] and were then held to a goalless draw by Millwall, who had yet to win a match during the season.

[23] Gilligan ended the team's scoreless run against Exeter City on 18 October and Peter Glen added a second goal to secure a 2–0 victory.

[25][26] On 1 November, Gillingham hosted Swindon Town, who had won every one of their first nine games;[27][28] the visit of the league leaders attracted an attendance of 12,000, the largest of the season at Priestfield Road.

Although Gillingham had been defeated, the reporter for The Daily Telegraph wrote that they had "fully upheld their reputation as particularly dangerous opponents on their own ground" and that there had been "little, if anything, to choose between two thoroughly efficient sides".

[40][41] Bailey kept a third consecutive clean sheet as Gillingham secured a 0–0 draw away to Queens Park Rangers in their final match of the calendar year,[42] after which they were 12th in the league table.

[13][51] A goalless draw at home to Cardiff City on 28 February meant that Gillingham had not won any matches during the month,[13][50] and as a result had slipped back to 11th in the table.

[13][56] The team's form remained inconsistent: they lost 2–0 away to Merthyr Town, who were bottom of the table, on 21 March,[57] but a week later beat fifth-placed West Ham United 3–1.

Despite the return of Hafekost, the team's leading goalscorer of the season so far,[13] Gillingham again failed to score against Norwich City on 10 April; the game ended in another 0–0 draw.

[64][65] Goals from Glen and Gilligan gave Gillingham a 2–0 win; the correspondent for The People wrote that the result was no surprise and that Nunhead's forwards were "seldom allowed to become dangerous".

[66] In the fifth and final qualifying round, Gillingham played fellow Southern League Division One team Watford and won 1–0 with a goal from Abel Lee.

[67] The teams from the Football League entered the competition in the first round proper and Gillingham were drawn to play Blackpool of the Second Division; the attendance of 10,581 was one of the largest of the season at Priestfield Road.

[70][71] The writer for the Sunday Dispatch said that Gillingham "gave a very pluck[y] display" and that if their forwards had taken advantage of playing with the wind behind them in the first half the result could have been different.

[75] Buoyed by the increased level of attendance at Priestfield Road during the 1913–14 season, Gillingham's board of directors secured a bank loan of £1,570 (equivalent to £190,000 in 2023)[76] to fund the building of a new grandstand.

[1][77][78] Only a few weeks after the new stand was opened to the public, however, it suffered major damage due to gale-force winds, including having the roof torn off.

[79][80] Despite the outbreak of the First World War in July 1914, the 1914–15 football season took place as normal;[81][82] Gillingham finished 20th out of 20 teams in the Southern League Division One.

[3] Owing to the escalation of the war and growing public sentiment that continuing sporting events as normal was not appropriate, the Southern League, along with all other major football competitions in England, was abandoned in 1915 and did not resume for four years.