At the start of the 1939–40 English football season, Gillingham F.C. competed in the Southern League Division One. It was the second season of the team's second spell in the league; the club had lost its place in the national Football League in 1938 after eighteen seasons. Prior to the season, the club appointed Archie Clark as player-manager. After Gillingham had played three matches, the Southern League season was abandoned due to the outbreak of the Second World War; following two months of inactivity, Gillingham joined the Kent Regional League, competing against mostly minor local teams. This competition was also abandoned without being completed and Gillingham did not play another competitive match for four years.

Background and pre-season After playing in the Southern League since 1894, Gillingham were among the founder members of the Football League Third Division in 1920, which was renamed the Third Division South when a parallel Third Division North was created a year later. After finishing in the bottom two places in the 1937–38 season, requiring them to apply for re-election to the League, Gillingham were voted out of the competition. The club returned to the Southern League and finished third in its First Division in the 1938–39 season. Gillingham applied to re-join the Football League at the first opportunity, but the application was rejected.

In August, Gillingham appointed former Everton and Tranmere Rovers player Archie Clark as player-manager, replacing Bill Harvey in the managerial role.

Southern League Division One Gillingham's first game of the season was away to Tunbridge Wells Rangers and resulted in a 2–0 victory.

On 2 September, Gillingham lost 1–0 away to Worcester City. The following day, Britain entered the Second World War and the Southern League season was quickly abandoned.

Southern League match details Key

In the result column, Gillingham's score is shown first H = Home match A = Away match

pen. = Penalty kick o.g. = Own goal

Results DateOpponentsResultGoalscorersAttendance25 August 1939Tunbridge Wells Rangers (A) 2–0Wilson, Rowleynot recorded30 August 1939Newport County reserves (H) 4–3 Rowley (3), Scottnot recorded2 September 1939Worcester City (A) 0–1 not recorded

Kent Regional League (Eastern Group) After the suspension of major competitions, a number of temporary leagues were formed; due to government-imposed travel restrictions, these competitions were organised on a localised basis. Gillingham joined the Kent Regional League (Eastern Group) with other teams from the eastern part of the county of Kent; Tunbridge Wells Rangers were the only other Southern League team to join, but they subsequently withdrew. The other clubs had all begun the season in the lower-level Kent League with the exception of Shorts Sports, who were a works team from Rochester. Teams often fielded guest players and statistics from the competition are regarded as unofficial and not part of players' career records.

Gillingham's first match for two months took place on 4 November away to Margate and resulted in a 1–1 draw.

Gillingham's final match of the season was a 7–0 victory away to Maidstone United; the away match with Ramsgate Grenville was one of a number of scheduled games which were never played.

Kent Regional League match details Key

In the result column, Gillingham's score is shown first H = Home match A = Away match

pen. = Penalty kick o.g. = Own goal

Results DateOpponentsResultGoalscorersAttendance4 November 1939Margate (A)1–1Hicksonnot recorded18 November 1939Lloyds Paper Mills (H)4–0Day (2), Campbell, Herbertnot recorded25 November 1939Canterbury Waverley (A)7–4Scott (2), Walsh (2), Hickson, Lee, Pipernot recorded2 December 1939Dover (H)5–2Walsh (3), Fowler, Leenot recorded9 December 1939Sittingbourne (A)5–1Hickson (2), Walsh (2), Herbertnot recorded16 December 1939Margate (H)10–0Hickson (5), Herbert (2), Campbell, Lee, Walsh (pen.)not recorded26 December 1939Maidstone United (H)5–1Herbert (2), Lee (2), Goldingnot recorded6 January 1940Canterbury Waverley (H)3–0Wilson (pen.), Lee, Hicksonnot recorded17 February 1940Shorts Sports (H)4–3Jackson (2), Lee, Hicksonnot recorded24 February 1940Aylesford Paper Mills (H)7–2Lee (3), Keenan (2), Wilson, Herbert (pen.)not recorded9 March 1940Dover (A)5–3Wilson (2), Herbert, Hickson, Leenot recorded16 March 1940Ramsgate Grenville (H)3–3Herbert (2), Leenot recorded22 March 1940Ashford Town (A)3–4Hickson (2), Herbertnot recorded23 March 1940Ashford Town (H)6–3Herbert (3, 2 pens.), Lee, Golding, Hicksonnot recorded6 April 1940Aylesford Paper Mills (A)3–1Hickson (2), Leenot recorded10 April 1940Shorts Sports (A)0–2not recorded20 April 1940Lloyds Paper Mills (A)7–2Hickson (4), Batchelor (2), Herbertnot recorded27 April 1940Sittingbourne (H)6–0Wilson (3), Bryant (2), Batchelornot recorded1 May 1940Maidstone United (A)7–0Hickson (3), Lee (3), Woodnot recorded

Aftermath The Kent Regional League season was abandoned with a number of games unplayed. Gillingham effectively ceased operations and did not play another competitive match until 1944.

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