August–December

The team's first game of the season was an away match against Newport County; Haylock, Pearce, Pritchard and Quow all made their debuts in a 2–1 victory. Weatherly scored the team's first goal of the season and Dave Shearer scored the winner.^[24] The first home league game took place at Priestfield Stadium seven days later against Bristol City in front of a crowd of 4,185, the largest attendance for Gillingham's opening home game since 1981.^[25] Shearer scored in a 1–1 draw and then got the only goal of the game away to Rotherham United to give Gillingham the win and seven points out of a possible nine from the first three games of the season.^[24] The team's unbeaten run in the league extended to six games with a goalless draw against Middlesbrough and 2–0 wins against both York City and Brentford, before the first defeat of the season came against Mansfield Town.^[24] Colin Greenall, a highly rated defender who had been signed from Blackpool for £40,000 at the start of September, made his debut in the Middlesbrough game.^[24][26]

A game against Chester City which should have taken place in late September was postponed because of an outbreak of illness among the opposing players.^[27] Following the defeat at Mansfield, Gillingham were unbeaten for the next seven league games, winning five and drawing two. Shearer scored in four consecutive games, taking his total for the season to seven goals.^[24] The team had no game on October 11, as the scheduled match away to AFC Bournemouth was postponed because Dorset Constabulary did not have sufficient manpower to police both the match and the Conservative Party Conference, which was taking place in the town.^[9] The unbeaten run came to an end with a 2–0 defeat away to Doncaster Rovers on 7 November, but the team then won 3–1 against fellow promotion-chasers Notts County, a game in which Shearer scored twice.^[28] Despite a defeat away to Wigan Athletic on 29 November, in a match which was unusually played in the morning to avoid a clash with an international rugby league match taking place in the town,^[29] Gillingham ended the month in second place in the league table.^[24]

The postponed game away to AFC Bournemouth was played on 2 December; since the start of the season Bournemouth had won every league game played at their home stadium, Dean Court. Gillingham, however, secured a 2–0 win with goals from Martin Robinson and Pritchard, which took the team to the top of the Third Division table.^[30][31][32] In the next league game, Gillingham lost 3–0 away to mid-table Bolton Wanderers, a game in which Tony Cascarino was sent off.^[33] Gillingham bounced back from the defeat with a 4–1 victory over Bristol Rovers which ensured they were back on top of the division heading into the Christmas period.^[34] The team ended 1986 with two games on consecutive days; a draw with Fulham on Boxing Day followed by a defeat to Swindon Town the next day left Gillingham in third place in the Third Division table going into the new year.^[24] The game against Swindon, regarded by fans as one of Gillingham's rivals since the 1970s,^[35] drew an attendance of 9,982, more than 4,000 higher than that at any other match at Priestfield to that point of the season.^[24]

January–May

Gillingham began 1987 with a home win over Walsall on New Year's Day. Pritchard scored a hat-trick before half-time in a 4–0 victory which brought the team to within one point of league leaders Middlesbrough, who lost away to York City.^[13][36] After this the team lost four of their next six matches and increasingly began to lose touch with the teams at the top of the league; following a defeat against Brentford on 21 February Gillingham had dropped to sixth in the table.^[24] In February, Shearer sustained an injury, so Peacock signed Colin Gordon on loan from Wimbledon; the striker scored twice in four games before returning to his parent club.^[37] In the same month, goalkeeper Phil Kite joined from Southampton, initially on loan, after Ron Hillyard was injured; the transfer was made permanent after some impressive performances and Kite retained the goalkeeping position for the remainder of the season, playing in every match.^[38] Midfielder Steve Jacobs, who had joined the club from Charlton Athletic in December, made his debut in February and played six consecutive league games, but then did not play again for over a month.^[39][40]

In March, Gillingham won three consecutive league matches for the first time since November, beating Carlisle United, Darlington, and Bournemouth.^[24] Shearer, in his first start after his injury, scored twice against Carlisle. Against Darlington, Cascarino became the second Gillingham player of the season to score a hat-trick, with three goals in a 4–1 victory. The Bournemouth game, played on Easter Monday, drew the club's largest home crowd since the Swindon game in December.^[24] Experienced defender Les Berry joined Gillingham from Brighton & Hove Albion during March; he made his debut in an away defeat to Bury at the end of the month and was an ever-present for the remainder of the season.^[41]

The team began April with two consecutive wins against Doncaster Rovers and Blackpool but then lost to Walsall.^[24] On his return to the team against Walsall, Jacobs was sent off for retaliating after being fouled by an opponent. He did not play in any of the team's remaining games and left the club at the end of the season.^[39] A win against Bristol Rovers on 25 April left Gillingham in fifth place in the league table, but the next three games produced two draws and one defeat, after which the team had fallen to seventh position with one game remaining.^[24] At the start of the season, the Football League had introduced a new play-off system, under which the teams which finished just below the automatic promotion places in the Second, Third, and Fourth Divisions would have the opportunity to compete for one further promotion place; in the Third Division this meant that the teams finishing third, fourth, and fifth in the final table would take part.^[42][43] To finish in fifth position and qualify for the play-offs, the team needed to defeat Bolton Wanderers on the last day of the league season and needed both Bristol City and Notts County not to win. A goal from Cascarino secured a 1–0 win, and as both of their rivals were held to 1–1 draws, Gillingham clinched a play-off place.^[44][45] Cascarino's goal was his 16th of the season in Third Division matches, tying him with Shearer as the club's top goalscorer in league matches.^[46]

Match results

Key

Results^[24]

Partial league table

Play-offs

Under the original format of the play-offs, the club which had finished immediately above the automatic relegation places in the Second Division competed with the three clubs which had finished immediately below the automatic promotion places in the Third Division for a place in the second tier of English football for the following season.^[48] At the semi-final stage, Gillingham were paired with Sunderland, who had finished the season in 20th place in the Second Division, in a two-legged tie. Sunderland took a 1–0 lead in the first half of the first leg at Priestfield, but Cascarino scored a hat-trick after the interval to put Gillingham 3–1 up. A late goal for Sunderland made the final score 3–2 to Gillingham.^[49] Three days later at Roker Park in Sunderland, Pritchard scored for Gillingham inside the first five minutes to give his team a two-goal lead on aggregate, but Sunderland then scored twice. In the second half, Cascarino made the score 2–2 on the day and 5–4 on aggregate, but Sunderland got a third goal in the final minute to bring the aggregate scores level at 5–5 and send the game into extra time. Both teams got one more goal in the extra period, at the end of which the score was 6–6 on aggregate, but Gillingham progressed to the final because they had scored more away goals.^[50][51]

The final against Swindon Town was also played over two legs and again the first match took place at Priestfield, where the attendance of 16,775 was the largest crowd of the season at the stadium.^[28] Violence broke out before the game between the two sets of fans and two British Transport Police officers were injured.^[52] In the match itself, Swindon were "superior in all departments except the telling ones – finishing and goalkeeping" according to David Powell of The Times.^[53] The game remained goal-less until the 81st minute when Smith scored following a free kick from Quow to give Gillingham a single-goal lead going into the second leg.^[53] Three days later at Swindon's County Ground, Elsey volleyed the ball into the goal to give Gillingham a two-goal lead on aggregate, but goals from Peter Coyne and Charlie Henry for Swindon made the result on the day 2–1 to Swindon and the aggregate score across the two legs 2–2.^[54] Unlike in the semi-final, away goals were not used as a tiebreaker in the final; instead the rules stated that, in the event of the scores finishing level after the two legs, a replay would take place at a neutral stadium.^[55] Robert Armstrong of The Guardian described the second leg as "an epic battle, in the best Anglo-Saxon tradition of the knockout competition".^[54] The replay took place at Selhurst Park, home of Crystal Palace. It was Gillingham's 63rd match of the season, a new record for the highest number of games the team had played in a season since joining the Football League.^[56] Swindon took the lead after only two minutes following a defensive error by Gillingham.^[56] Although Gillingham were the stronger team in the second half, they could not manage to score a goal, and Steve White of Swindon got his second goal of the match in the second half. Despite further pressure on their goal, Swindon held on for a 2–0 victory and promotion to the Second Division.^[56][57]

Match results

Key

Results^[28]

FA Cup

As a Third Division team, Gillingham entered the 1986–87 FA Cup in the first round, where they were drawn to play Kettering Town of the Football Conference, the highest level of non-League football. Gillingham won 3–0 with goals from Robinson, Hinnigan and an own goal from a Kettering player.^[58] In the second round, Gillingham played another non-League team, Chelmsford City of the Southern League. Cascarino scored twice in a 2–0 victory.^[59] Gillingham's third round opponents were fellow Third Division team Wigan Athletic. The game was twice postponed due to heavy snow in the south of England, the club at one point hiring a police Land Rover to pick up players who lived in outlying areas after the football authorities initially refused the second postponement.^[60][61] After that decision was reversed, the match finally took place on 19 January. Greenall scored a goal from a penalty kick but Wigan scored twice to end Gillingham's cup run.^[62]

Football League Cup

Gillingham entered the 1986–87 Football League Cup in the first round, being drawn against Northampton Town of the Fourth Division. The first round was played over two legs; Gillingham won the first leg at Priestfield 1–0 and drew the second leg at the County Ground 2–2 for a 3–2 aggregate win.^[63] In the second round, Gillingham were drawn against the reigning cup-holders, Oxford United of the First Division.^[64] The first leg was played at Oxford's home ground, the Manor Ground, where Gillingham were comprehensively outplayed, losing 6–0. Republic of Ireland international striker John Aldridge scored four of the Oxford goals.^[65][66] This was the most goals conceded by Gillingham in a match since a 7–1 defeat by York City in November 1984.^[67] Although Gillingham managed to hold their First Division opponents to a 1–1 draw at Priestfield in the second leg, they lost 7–1 on aggregate and were eliminated from the League Cup.^[68]

Associate Members' Cup

The 1986–87 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 were drawn with Notts County of the Third Division and Northampton Town of the Fourth and won both games without conceding a goal, defeating Notts County 5–0 away from home and Northampton 1–0 at Priestfield Stadium.^[69][70] The team thus qualified for the first round, where they were paired with Colchester United of the Fourth Division. Goals from Smith and Cascarino gave Gillingham a 2–0 win in front of 1,984 fans, the smallest crowd to attend a match at Priestfield during the season.^[28][71] In the southern section quarter-final, Gillingham played Port Vale; the match finished 3–3 after extra time, meaning that a penalty shoot-out was required to determine which team would progress to the next round. Gillingham scored all five of their penalties and then Hillyard saved Port Vale's final penalty meaning that Gillingham won the shoot-out 5–4.^[72][73] Now just two wins away from the final, Gillingham's next opponents were fellow Third Division promotion challengers Bristol City; it was the second consecutive season in which the two teams had met at this stage of the competition.^[74] The attendance of 10,540 at Bristol City's home stadium, Ashton Gate, was the largest crowd in front of which Gillingham had played up to that point in the season.^[28] Gillingham lost 2–0, meaning that their participation in the Associate Members' Cup was ended by Bristol City for the second season in a row.^[74]