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[Creeperopolis]

During the 1998–99 English football season, Gillingham F.C. competed in the Football League Second Division, the third tier of the English football league system. It was the 67th season in which Gillingham competed in the Football League, and the 49th since the club was voted back into the league in 1950. The club signed two new forwards, each for a new club record transfer fee, but started the season in poor form, winning only one of the first eight league games. The team then went on a much-improved run, being undefeated for 17 league games, and began challenging for promotion to the Football League First Division. Gillingham finished the regular season in fourth place in the Second Division, qualifying for the play-offs for promotion to the First Division. After defeating Preston North End in the semi-finals, they played Manchester City at Wembley Stadium in the final. Gillingham were 2–0 up with less than ten minutes remaining but conceded two late goals, and Manchester City won the subsequent penalty shoot-out to gain promotion.

Gillingham also reached the southern section semi-final of the Football League Trophy, but were eliminated from both the FA Cup and the Football League Cup in the first round. The team played 56 competitive matches, winning 26, drawing 16 (including the play-off final), and losing 14. Carl Asaba was the team's leading goalscorer with 22 goals. Paul Smith made the most appearances during the season, playing in 54 of the team's 56 matches. The highest attendance recorded at the club's home ground, Priestfield Stadium, was 10,400 for the visit of Manchester City. Despite leading the team to the play-off final, manager Tony Pulis was dismissed from his job shortly afterwards amid allegations of gross misconduct. He sued the club for unfair dismissal and accepted an out-of-court settlement.