Duncan Alan Jupp is a former professional footballer who played as a defender. Born in England, he earned nine caps with the Scotland U21 national team.
Colin David Powell is an English retired professional footballer, active during the 1970s and 1980s. He spent the bulk of his career with Charlton Athletic.
Albert Herbert Hoskins was an English football forward and football manager, who managed Wolverhampton Wanderers and Gillingham.
Colin Mark Weatherly is an English retired footballer. He spent his entire professional career with Gillingham, where he played in 457 Football League matches, a club record for an outfield player.
Stephen Lovell is a Welsh former professional footballer and manager. He is currently manager of Herne Bay.
Neil Smillie is an English former professional football player and manager. He played for a number of clubs, and appeared in the 1983 FA Cup final for Brighton & Hove Albion.
Stephen Allan John Crabbe is an English former professional footballer. He played for six Football League clubs, with his most successful spell coming at Gillingham.
Karl William Elsey is a Welsh former professional footballer. His clubs included Swansea City, Queens Park Rangers, Newport County, Cardiff City, Gillingham, Reading and Maidstone United. In total he made over 450 Football League appearances.
Kevin Johnston Bremner is a Scottish former professional footballer who played as a striker. He made nearly 450 appearances in the English and Scottish Football Leagues, representing ten different clubs.
Michael Sydney Trusson is an English former professional footballer. He made over 400 appearances in a fifteen-year professional career, and later worked in sports marketing and as a scout.
During the 1920–21 English football season, Gillingham F.C. competed in the Football League for the first time. The team had previously played in Division One of the Southern League, but in 1920 the Football League added the Third Division to its existing set-up by absorbing the entire Southern League Division One. The club appointed Robert Brown as manager, but the arrangement turned out to be only a casual one and he accepted another job before the season started. Under his replacement, John McMillan, Gillingham's results were poor, including a spell of over three months without a league victory, and at the end of the season they finished bottom of the league table.
Colin Kenneth Gordon is an English former footballer born in Stourbridge, Worcestershire, who played as a striker.
William Henderson (1878–1945) was a Scottish footballer who played as a full-back for various clubs in England at the turn of the 20th century.
Timothy John Parkin is an English former footballer. A defender, he made 422 league appearances in a 14-year career in the English Football League, and also spent two years playing in Sweden.
Richard David Bowman is an English former professional footballer.
During the 1986–87 English football season, Gillingham F.C. competed in the Football League Third Division. It was the 55th season in which the club competed in the Football League, and the 37th since the club was voted back into the league in 1950. Gillingham began the season strongly and were top of the Third Division table shortly before the mid-point of the season. The team's form declined in the second half of the season; to qualify for the play-offs for promotion to the Football League Second Division, the team needed to win their final game and both Bristol City and Notts County had to fail to win theirs. A victory over Bolton Wanderers, combined with both the other teams being held to draws, meant that Gillingham finished in fifth place and qualified for the play-offs. After beating Sunderland in the semi-finals, Gillingham faced Swindon Town in the final. The two teams drew 2–2 on aggregate, necessitating a replay at a neutral venue, which Swindon won 2–0 to claim a place in the Second Division.
Mark Whitlock is an English retired footballer. Primarily a centre back, Whitlock played initially for Hampshire-based club Southampton, before moving to local rivals Bournemouth in 1986, Reading in 1988, and Aldershot in 1990.
The 1987 Football League Third Division play-off final was an association football match contested by Gillingham and Swindon Town over two legs on 22 and 25 May 1987, followed by a replay on 29 May, to determine which club would play the next season in the Second Division. Gillingham had finished in fifth place in the Third Division while Swindon finished third. They were joined in the play-offs by fourth-placed Wigan Athletic and Sunderland, who had finished 20th in the division above. Gillingham defeated Sunderland in their semi-final on away goals and Swindon defeated Wigan in the other semi-final. Swindon had previously had two spells in the Second Division, but Gillingham were aiming to reach the second tier of English football for the first time in their history. The 1986–87 season was the first in which the teams who had missed out on automatic promotion had the opportunity to compete in play-offs for a further promotion place.
During the 1988–89 English football season, Gillingham F.C. competed in the Football League Third Division, the third tier of the English football league system. It was the 57th season in which Gillingham competed in the Football League, and the 39th since the club was voted back into the league in 1950. Gillingham began the season well, with two wins in the first three Third Division games, but then lost ten consecutive league games to slip close to the bottom of the league table. In late October, after the eighth of these defeats, Paul Taylor was dismissed as the club's manager and replaced by Keith Burkinshaw. The new manager could not significantly improve the team's performances, resigning in April with Gillingham bottom of the table. Former Gillingham player Damien Richardson ended the season as the club's manager. Gillingham finished the season 23rd out of 24 teams in the division and were relegated to the Fourth Division.
During the 1937–38 English football season, Gillingham F.C. competed in the Football League Third Division South, the third tier of the English football league system. It was the 18th season in which Gillingham competed in the Football League. The team won only three times in nineteen Football League matches between August and December; in November and December they played six league games and lost every one without scoring a goal, leaving them bottom of the division at the end of 1937. Although Gillingham's performances improved in the second half of the season, with seven wins between January and May, they remained in last place at the end of the season, meaning that the club was required to apply for re-election to the League. The application was rejected, and as a result the club lost its place in the Football League and joined the regional Southern League.
