August–December

Gillingham's first game in the Fourth Division since 1974 took place at their home ground, Priestfield Stadium, on 19 August against Aldershot.^[15] Johnson made his debut,^[6] but Pulis was absent after being injured in a friendly.^[16] With injuries also ruling out Alan Walker, Tim O'Shea, and Brian Clarke, and further new signings not yet completed,^[17] Richardson was forced to select teenagers Ricky Pearson, Peter Beadle, Ivan Haines, Russell Norris, and Steve Thompson, the last two of whom were playing their first professional matches.^[18][19] The match finished in a goalless draw, as did the next league game away to Doncaster Rovers.^[15] Following a Football League inquiry, it was ruled that Gavin was now a Leicester player but that as a form of compensation he should return to Gillingham on loan for the duration of the 1989–90 season;^[8][20] he played for the first time since this ruling in the home game against Scunthorpe United, Gillingham's third league game of the season.^[21] Mike Trusson, a midfielder signed from Brighton & Hove Albion,^[22] made his debut in the same game.^[21] Gillingham lost the match 3–0, meaning that after three league games they were yet to score a goal in the Fourth Division.^[15] Peter Heritage, a forward signed from Hythe Town of the Southern League for a transfer fee of £30,000 (equivalent to £80,000 in 2021),^[23] made his debut against Scunthorpe;^[21] it was his first professional match at the age of nearly 29.^[24] The team's goalless run ended with a 2–1 win away to Hartlepool United on 9 September, Heritage scoring the winning goal, but the team then drew 0–0 with Burnley and lost 3–0 to Carlisle United.^[15] After six games, Gillingham were 18th of 24 teams in the league table.^[25]

Gillingham next played Southend United, who were top of the table and unbeaten.^[26] Having scored only two goals in the previous six league games, Gillingham won 5–0, the team's biggest win for two years.^[27] The next two games resulted in a 1–1 draw away to Peterborough United and a 1–0 win away to Halifax Town, Steve Lovell scoring both times,^[15] which took Gillingham up to 9th place.^[28] The team slipped back to 15th, however, after losing both their next two games without scoring a goal;^[15][29] captain Walker was absent for both games after being injured again.^[30] He returned to the team for a 3–0 win over Chesterfield on 21 October;^[31] Hillyard made his 618th appearance for Gillingham in that game, a new club record.^[32] It was the first of five consecutive league victories for the team; Gillingham ended October with a 1–0 win at home to Rochdale and won their first four league games of November, defeating Scarborough, Lincoln City, and Torquay United.^[15] The results took Gillingham up to 6th in the table, putting them in the promotion play-off places.^[33][34] The winning run came to an end with a 3–3 draw at home to Colchester United on 24 November, and Gillingham then lost in the Fourth Division for the first time in nearly two months when they were defeated 1–0 by York City on 9 December.^[15]

A week later, Mark O'Connor, a midfielder signed from AFC Bournemouth for £70,000 (equivalent to £190,000 in 2021), made his debut away to Exeter City;^[35] the game resulted in a second consecutive defeat.^[15] Ten days later, Gillingham played their first Football League match against near-neighbours Maidstone United,^[36] who had gained promotion from the Football Conference at the end of the previous season.^[37] Maidstone had competed in non-League football throughout their history,^[38] and such was the interest in the first Football League match between two teams from the county of Kent that the game drew an attendance of 10,412. It was Gillingham's largest home crowd for more than two years, and the start of the match had to be delayed to allow all the spectators into the stadium.^[36] Maidstone manager Keith Peacock had held the same post at Gillingham for six years until he was dismissed in 1987, a decision which led to public demonstrations by angry supporters, and he included five former Gillingham players in his team for the game.^[36][39] Maidstone took a two-goal lead in the second half and Mark Beeney, one of their former Gillingham players, saved a penalty kick from Lovell. Walker scored for Gillingham with two minutes remaining, colliding with the goalpost and knocking himself unconscious in the process, but Maidstone retained their lead and won the match.^[36] Pulis made his long-delayed debut in the team's final game of 1989,^[40] a 1–0 victory over Wrexham which took Gillingham up from 11th to 8th in the table, two points below the play-off places.^[41]

January–May

Gillingham began the new year with an away game against Hereford United on 1 January;^[15] having scored his first goal for the club two days earlier, Johnson scored his second in a 2–1 victory.^[21] They would prove to be the only two goals he scored in nearly 80 games with the club.^[42] The team achieved a second consecutive victory with a 3–1 win over Doncaster Rovers,^[15] after which they were once again in the play-off places. The last two league games of January resulted in a defeat to Aldershot and a draw with Hartlepool United, in both of which the team failed to score any goals; Lovell, the team's leading goalscorer, had scored only once in his last six league games.^[31] His first goal of 1990 gave Gillingham a 2–1 win over Burnley on 13 February to keep Gillingham 8th in the table; Pulis was substituted after being injured again and would miss the next four games.^[21][43]

Following the victory over Burnley, Gillingham failed to score in a further three matches, which resulted in two more goalless draws and a defeat away to Colchester United.^[15] The goalless run ended when Gillingham won 2–1 on 27 February against Carlisle United, who were top of the table going into the game.^[44] The result took Gillingham back up to 6th place,^[45] and they remained there after they began March with a 1–0 win at home to Cambridge United.^[46] Gavin, who had been restored to the starting line-up two games earlier after several games as a substitute,^[21] scored the only goal of the game in the first half; it would prove to be the only goal he scored in 39 matches during his loan spell.^[47] Following the victory, Gillingham were only two points below the three automatic promotion places and, although they once again failed to score in the next game against Peterborough United, another goalless draw reduced the gap to a single point.^[48] On 16 March, Gillingham beat Halifax Town 3–1 in a Friday evening game to climb to 3rd place,^[49] although after the next day's games they had fallen back to 6th.^[50] Following that victory, however, the team lost their next six games, a run during which they scored only a single goal in over nine hours of football.^[15] Beadle returned to the team as a substitute in the 2–0 defeat to Torquay United on 7 April; the teenaged forward had not played for the first team since the signing of Heritage,^[21] but was recalled from a loan spell at Margate following an injury to Trusson which would keep the midfielder out for the rest of the season.^[51][52] By the time Gillingham lost 1–0 to Hereford United on 14 April, their sixth consecutive defeat and fourth without scoring a goal, they had fallen to 14th in the table.^[53]

On 16 April, Gillingham played their away match with Maidstone, who were 4th in the table and challenging for promotion;^[54] the crowd of 5,003 was Maidstone's largest to date for a home league game.^[54] A goal from Heritage early in the first half gave Gillingham a victory over their rivals,^[55] which took Gillingham back up to 12th place.^[56] In the next game, Beadle's first professional goal secured a 1–1 draw against Exeter City,^[57] but this was followed by a defeat to Wrexham.^[15] In the last game of April, at home to Lincoln City, Gillingham were winning until the last minute of the game but then conceded an equalising goal.^[58] This left Gillingham nine points off 7th place and therefore, with two games remaining and a maximum of six points available, unable to finish in the play-off positions.^[59] Gillingham's last game of the season was away to Scarborough;^[15] Lovell scored the only goal of the match in the last 10 minutes to give his team victory, the third consecutive game in which he had scored. The result meant that Gillingham finished the season 14th in the Fourth Division, nine points below the play-off places.^[33]

Match details

Key

Results^[15]

Partial league table

FA Cup

As a Fourth Division team, Gillingham entered the 1989–90 FA Cup in the first round, where they were drawn to play Welling United of the Football Conference. The initial match at Priestfield ended in a goalless draw,^[61] necessitating a replay four days later at Welling's Park View Road ground. A goal from Welling's Mark Hone in the first half was enough to give the semi-professional team victory and eliminate Gillingham from the FA Cup.^[62] It was the first time that Welling had beaten Football League opposition in the FA Cup in their history; Paul Newman of The Times described Gillingham's play in the second match as "ragged" and Welling manager Nicky Bridgen told the press "I wouldn't want to put Gillingham down but, to be honest, getting a draw on Saturday was no more difficult than drawing at somewhere like Telford in the Conference. We got what we deserved."^[63]

Football League Cup

As a Fourth Division team, Gillingham entered the 1989–90 Football League Cup in the first round and were paired with Leyton Orient of the Third Division. Gillingham lost the first leg of the two-legged tie 4–1 at Priestfield and the second 3–0 at Orient's Brisbane Road ground and were eliminated from the competition by an aggregate score of 7–1.^[65][66]

Associate Members' Cup

The 1989–90 Associate Members' Cup, a tournament exclusively for Third and Fourth Division teams, began with a preliminary round in which the teams were drawn into groups of three, contested on a round-robin basis. Gillingham's group also included fellow Fourth Division teams Southend United and Cambridge United. In the first match of the group, Southend defeated Gillingham 1–0.^[67] Three weeks later, Gillingham beat Cambridge 2–0 at Priestfield;^[68] goalkeeper Harvey Lim, who had recently joined the club as back-up to Hillyard after a spell playing in Sweden,^[69] made his debut.^[40] The match drew an attendance of 1,044, the lowest of the season at Priestfield.^[40] The final match of the group resulted in a draw between Southend and Cambridge, meaning that Gillingham finished second in the group and progressed to the first round proper.^[70] Their opponents were Bristol Rovers of the Third Division, who won 1–0 to end Gillingham's participation in the competition.^[71]