During the 1987–88 English football season, Gillingham F.C. competed in the Football League Third Division. It was the 56th season in which the club competed in the Football League, and the 38th since the club was voted back into the league in 1950. In the previous season, Gillingham had qualified for the final of the play-offs for promotion to the Football League Second Division but had been defeated. The team began the new season strongly, including winning matches 8–1 and 10–0 on consecutive Saturdays, but their performances quickly declined and by December the team had slipped down the league table. After a heavy loss to Aldershot in the last game of 1987, manager Keith Peacock was dismissed from his job and replaced by his former assistant Paul Taylor, a decision which was extremely unpopular with the club's supporters. Although the team's performances improved in the second half of the season, briefly bringing them close to a potential play-off place, their form declined once again and they finished the season 13th in the 24-team division, the same position as when Peacock lost his job.
During the season, Gillingham also reached the third round of the FA Cup and the second round of the Football League Cup, but were eliminated from the Associate Members' Cup at the earliest stage. The team played 55 competitive matches, winning 17, drawing 17, and losing 21. Steve Lovell was the club's leading goalscorer, with 27 goals in all competitions, three times as many as any other player. He also made the most appearances, playing in all of the team's 55 matches; two other players each appeared over 50 times. The highest attendance recorded at the club's home ground, Priestfield Stadium, was 9,267 for an FA Cup match against Birmingham City.
Background and pre-season
The 1987–88 season was Gillingham's 56th season playing in the Football League and the 38th since the club was elected back into the League in 1950 after being voted out in 1938. It was the club's 14th consecutive season in the Football League Third Division, the third tier of the English football league system, since the team gained promotion from the Fourth Division as runners-up in 1974. In the 13 seasons since then, the team had achieved a best finish of fourth place, one position away from promotion to the Second Division, a feat achieved in both the 1978–79 and 1984–85 seasons. In the 1986–87 season, Gillingham had finished fifth, qualifying for the newly introduced play-offs for the third promotion place, but lost to 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 ensure that Gillingham would again be playing in the Third Division the following season.
Keith Peacock was the club's manager for a seventh season, having been appointed in July 1981. Paul Taylor continued in the role of assistant manager, having been appointed at the same time as Peacock. Bill Collins, who had been with the club in a variety of roles since the early 1960s, held the post of first-team trainer, and John Gorman managed the youth team. Mark Weatherly was club captain, but for much of the early part of the season he was unable to play following an operation and subsequent injuries, so Colin Greenall served as captain on the field of play in his absence.