August–December

Gillingham began the season with an away game against Bury; Thomson scored on his debut but Gillingham lost 2–1.^[23] The first home game a week later against Bristol Rovers also resulted in a defeat.^[23] The team then gained three consecutive draws, and after five games were in 22nd position in the 24-team division.^[24] The match against Blackpool on 21 August included a controversial incident after Gillingham goalkeeper Bartram intentionally kicked the ball out of play so that an injured Blackpool player could receive medical treatment; when Blackpool took the throw-in they retained possession of the ball and scored the equalising goal. Manager Taylor was ejected from the technical area by the referee for entering the field of play and arguing with him over an unwritten rule that in such circumstances the player taking the throw-in returns the ball to the opposition.^[25][26]

Gillingham gained their first league win of the season at the sixth attempt on 4 September, defeating Oldham Athletic 2–1 after scoring two goals in the first six minutes of the match.^[23] The second was scored by Emmanuel Omoyinmi on his debut after joining on loan from West Ham United;^[27][28] the following week he scored again as Gillingham beat Oxford United 2–1 to move into the top half of the league table.^[29] The team then suffered another setback, losing to Preston North End. September ended with Gillingham in 15th place in the division.^[30]

On 9 October, Gillingham achieved their biggest win of the season, defeating Wrexham 5–1 at Priestfield; Robert Taylor scored a hat-trick inside the last half-hour of the game.^[23] Four games later, he repeated the feat, scoring all three goals in a 3–0 victory over Bristol City.^[23] That match marked Pulis's first appearance at Priestfield since his dismissal from the role of Gillingham manager, as he was now in charge of Bristol City; he received a standing ovation from the home fans.^[31] Taylor scored for the fifth consecutive game in a 4–1 win over Scunthorpe United on 23 November, taking his total to 15 goals in 15 Second Division games; two days later, he was signed by Manchester City for a transfer fee of £1.5 million, a new record for the highest fee received by Gillingham for a player.^[32][33] His initial replacement in the starting line-up was Rodney Rowe, a recent signing from York City.^[23][34] Despite losing their most prolific goalscorer, the team won their first three games without Taylor and were in fifth position in the league table after a 2–1 victory over Colchester United on 26 December.^[35] Gillingham's final match of 1999 resulted in a 2–0 defeat away to Wigan Athletic.^[28]

January–May

Gillingham signed two new players on 2 January, making them the first club in English professional football to conclude transfer business in the year 2000.^[36] Striker Iffy Onuora and midfielder Ty Gooden both joined from Swindon Town for a combined transfer fee of £200,000.^[36][37] It marked the start of a second spell at the club for Onuora, who had played for Gillingham between 1996 and 1998;^[38] he was a regular starter for the remainder of the season, with Rowe largely used only as a substitute.^[39] The team's first match of 2000 resulted in a 2–2 draw at home to Reading; Thomson gave Gillingham the lead in the 90th minute, but their opponents then equalised in injury time.^[23] The next two games both ended in defeat, and a goalless draw away to Chesterfield in the first match of February meant that the team had gone five games without a win.^[23] This left the team in seventh position in the table, albeit having played fewer games than all the teams above them.^[40]

On 5 February, Gillingham won a Second Division match for the first time in 2000, defeating Stoke City 3–0.^[23] It was the start of a run of four consecutive victories, which also included a win away to Preston North End, who had been top of the division going into the match.^[23][41][42] In the match against Preston, striker Carl Asaba, the team's top goalscorer in the previous season, made his first Football League appearance for nine months following a lengthy absence due to a hernia which required three operations.^[43] In March, Gillingham inflicted Bristol City's first home league defeat of the season.^[44] Gillingham lost consecutive away games against Colchester United and Wycombe Wanderers over the Easter weekend, but then beat Chesterfield 1–0, beginning an eight-game unbeaten run.^[23] This run included victories within four days over two of the other teams chasing promotion, Wigan Athletic and Burnley;^[45][46] following the latter win, Stephen Wood of The Times noted that Gillingham were "entering their best form at the perfect moment".^[46]

In the penultimate game of the season, Asaba scored Gillingham's third hat-trick of the season as the team beat Cardiff City 4–1.^[23] The result left Gillingham second in the table going into the final game, ahead of Burnley on goal difference;^[47] Gillingham would finish in that position and gain automatic promotion to the First Division if their result away to Wrexham matched or bettered that achieved by Burnley away to Scunthorpe United. Gillingham, however, lost 1–0, while Burnley won and thus moved above Gillingham into second place.^[48] Finishing third meant that Gillingham entered the play-offs for the final promotion place along with the three teams that finished below them.^[49] After the match, manager Taylor told the press "We are a bit sore, but we will be fine. It's up to me to earn my money and lift them. But I've got no doubts; I've always said that the spirit is first-class. Now it's going to be tested".^[48]

Match details

Key

Results^[28]

Partial league table

Play-offs

In the play-off semi-finals, Gillingham played sixth-place finishers Stoke City. In the first match of the two-legged tie, Stoke scored two goals in the first eight minutes. Although Gooden scored after 18 minutes, Stoke extended their lead to 3–1 in the second half. In the fifth minute of injury time, Hessenthaler scored to make the final score 3–2.^[51][52] Before half-time of the second leg, Stoke's Clive Clarke was sent off. Graham Kavanagh was also dismissed early in the second half, leaving Stoke with just nine players, after which Barry Ashby scored a goal for Gillingham to bring the aggregate score level at 3–3. In extra time, Onuora and Paul Smith scored further goals for Gillingham, who thus secured victory by a final aggregate score of 5–3.^[53][54][55] The crowd of 10,386 was the season's largest attendance at Priestfield.^[28]

Gillingham played Wigan Athletic in the final at Wembley Stadium. Gillingham took the lead in the first half when Wigan defender Pat McGibbon scored an own goal under pressure from Onuora.^[56][57] Wigan equalised shortly after half-time, and believed they had taken the lead when Southall blocked a shot from Wigan's Arjan de Zeeuw on the goal-line; the Wigan players believed that the ball had in fact crossed the line, but the referee ruled otherwise.^[57][2] With no further goals being scored by either team, the match went into extra time, during which Wigan took a 2–1 lead when Stuart Barlow scored a penalty kick.^[2] Gillingham scored two goals in the last six minutes through Butler and Thomson, both of whom had come on as substitutes, to win 3–2.^[2] Gillingham thus gained promotion to the second tier of English football for the first time in the club's 107-year history.^[2]

Match details

Key

Results^[28]

FA Cup

As a Second Division team, Gillingham entered the 1999–2000 FA Cup in the first round and were drawn to play away to Cheltenham Town, newly-promoted into the Football League Third Division from the Football Conference.^[58] The match at Cheltenham's Whaddon Road ground ended 1–1, necessitating a replay at Priestfield, which Gillingham won 3–2.^[59] In the second round, Gillingham played Darlington of the Third Division and won 3–1.^[60] Darlington were reinstated into the competition, however, when they were randomly selected from all the teams defeated in the second round to fill the vacant slot in the third round left by Manchester United's decision to withdraw from the FA Cup to take part in the 2000 FIFA Club World Championship.^[61] In the third round, Gillingham played away to Walsall of the First Division and held them to a 1–1 draw.^[62] The replay also finished 1–1, but unlike in the initial match the rules of the competition meant that extra time was played and Gillingham scored again to win 2–1.^[63][64]

Gillingham's opponents in the fourth round were Bradford City of the Premier League. Gillingham took a two-goal lead and, although Bradford scored in the last 15 minutes, Gillingham scored a third moments later and defeated their higher-level opponents 3–1^[65] to reach the last 16 of the FA Cup for only the second time in the club's history.^[66][67] It was also the first time that Gillingham had defeated a team from the highest division of English football in the FA Cup since 1908.^[66] In the fifth round, Gillingham played another Premier League team, Sheffield Wednesday. Wednesday scored in the first half and with 20 minutes of the match left, the score remained 1–0. Mark Saunders scored an equalising goal in the 70th minute and two minutes later Thomson scored to give Gillingham the lead. Southall added a third goal in the last 10 minutes and Gillingham won 3–1 to reach the quarter-finals of the FA Cup for the first time.^[68][69][70] For the third consecutive round, Gillingham faced Premier League opposition, this time Chelsea. Although Gillingham restricted their opponents to a single goal in the first half, the Premier League team scored a further four after the interval to make the final score 5–0.^[71][72][73]

Football League Cup

As a Second Division team, Gillingham entered the 1999–2000 Football League Cup in the first round and were drawn to play Brighton & Hove Albion of the Third Division. The first leg of the two-legged tie took place at the Withdean Stadium, Brighton's new home after a period spent sharing Priestfield Stadium,^[74] and resulted in a 2–0 win for Gillingham.^[75] The score was the same in the second leg, so Gillingham progressed to the second round with a 4–0 win on aggregate.^[76] In the next round Gillingham were paired with Bolton Wanderers of the First Division. The first leg at Priestfield ended in a 4–1 victory for the visitors and Bolton won the second leg 2–0 to secure a 6–1 aggregate victory and eliminate Gillingham from the competition.^[77]

Gillingham's participation in the League Cup had repercussions months after the team were eliminated from the competition. Omoyinmi, who was on loan from West Ham United, played in both matches against Bolton.^[28] When his loan ended, he returned to West Ham and played briefly as a substitute in their League Cup quarter-final victory over Aston Villa in December. As he had already played for a different team earlier in the competition, however, he was cup-tied and therefore not eligible to play for West Ham. Due to the presence on the pitch of an ineligible player, the teams were ordered to replay the match and West Ham lost the second game and were eliminated from the competition.^[78][79]

Football League Trophy

In the first round of the 1999–2000 Football League Trophy, a competition for Second and Third Division teams, Gillingham played Torquay United of the Third Division. With several regular players rested, Gillingham were defeated 3–0 by their lower-division opponents and were thus eliminated from the competition at the earliest stage.^[80] The attendance of 2,718 was the lowest of the season at Priestfield.^[28]

Match results

Key

Results^[28]