August–December

Gillingham began the Second Division season with a home game against Walsall and lost 1–0. The next three games all resulted in draws, after which Gillingham were in 18th place in the 24-team league table.^[16] The goalless draw against Bristol Rovers was marred by a brawl involving almost every player on the pitch, after which Gillingham's Barry Ashby and Adrian Pennock were both sent off, along with two Rovers players.^[17] Forward Carl Asaba made his debut in the 2–2 draw away to Blackpool on 29 August, having joined the club the previous day from Reading for a fee of £600,000 (equivalent to £1.2 million in 2021), another new club record.^[18][19] Gillingham achieved their first victory of the season at the fifth attempt, defeating Wrexham 4–0; Asaba scored his first goal since joining the club and the result took the team up to 12th in the table.^[20] Gillingham then lost their next two games, however, and again dropped to 18th.^[21]

The 1–1 draw against Colchester United on 12 September marked the start of an unbeaten run which would last for the remainder of the year. Two weeks later, Gillingham drew 1–1 away to Preston North End; before the game the players were presented to Sepp Blatter, president of world football's governing body FIFA, who was in attendance to open the National Football Museum, located at Preston's Deepdale stadium.^[22][23] The following game, a 2–2 draw at home to Macclesfield Town, was preceded by the arrival by helicopter of the club's new mascot, Tommy T. Trewblu.^[24] Between 20 October and 10 November, Asaba scored in five consecutive games, four of which resulted in victories, taking his total number of league goals to ten.^[25] Taylor, however, had only scored three league goals and was receiving negative reactions from some Gillingham supporters, who considered him out of shape and his large transfer fee a waste of money.^[11]

On 21 November, Gillingham played away to Manchester City, who were playing in the third tier of the English football league system for the first time in their history.^[26] The match, the first between the two clubs since 1908,^[27] resulted in a 0–0 draw and drew a crowd of 26,529, by far the largest crowd to watch a game involving Gillingham during the regular 1998–99 league season.^[25] Asaba scored the team's first hat-trick of the season on 19 December in a 4–0 victory over Notts County.^[25] Gillingham ended 1998 with a 1–1 draw at home to Millwall in front of 9,221 fans, the season's largest attendance at Priestfield Stadium to date.^[25][28] It was Gillingham's 16th consecutive league game without defeat,^[25] and left them sixth in the table.^[29]

January–May

The team won their first game of 1999, defeating Blackpool 1–0 to extend their unbeaten league run to 17 games and move up to fifth place.^[30] Seven days later, however, Gillingham were defeated in the league for the first time since September, losing 2–1 away to Walsall.^[25][31] In each of the next three matches the team scored three goals, resulting in two wins and a draw, which kept Gillingham in the top six of the table.^[25][32]

On 20 February, Asaba scored Gillingham's goal in a 1–1 draw with Colchester United but was then sent off for apparently head-butting Colchester's David Greene. Two weeks later, however, the red card was overturned by a special commission convened by the Football Association, the sport's governing body in England, based on evidence provided by police officers present at the game.^[33] In the final game of February, Gillingham recorded their best ever Football League win away from home when they beat Burnley 5–0 at Turf Moor; Taylor scored all five goals.^[34][35] It was the first time that a Gillingham player had scored as many goals in a single match since Fred Cheesmur scored six against Merthyr Town in 1930.^[36] In the following match, Taylor scored in the final minute to gain the team a draw against fellow promotion contenders Preston North End.^[37][38]

In March, Gillingham lost 4–1 to Wigan Athletic, the most goals conceded by the team in a single game during the season, but followed it up with a 4–0 win over Lincoln City. Kevin Lisbie, signed on loan from Charlton Athletic of the Premier League, scored in both games.^[39] Gillingham began the month of April with three consecutive victories; this included a win at home to Bournemouth with goals from Hessenthaler and Lisbie.^[40] The game was shown live by Sky TV, the first time the broadcaster had televised a game from Priestfield.^[41] After this run, Gillingham were fourth in the table, two places and three points below the automatic promotion positions.^[42] They then lost the next three games, however. Although Gillingham only dropped one position in the table as a result, they were now nine points below second place with three games remaining and a maximum of nine more points available.^[43] This run of defeats included Gillingham's first home defeat of the season, a 2–0 loss to Manchester City which drew an attendance of 10,400, the largest crowd to attend a match at Priestfield during the season.^[25][44] Gillingham defeated Oldham Athletic on 24 April and Stoke City a week later, scoring four goals each time. Four days after the second of these victories, Wigan Athletic lost to Wycombe Wanderers, meaning that Gillingham were guaranteed a place in the play-offs irrespective of the result of the final match of the regular season.^[45] Gillingham's final game resulted in a 1–0 win away against Notts County, Asaba scoring the only goal; this meant that they finished the regular season fourth in the table, seven points below second place.^[46]

Match details

Key

Partial league table

Play-offs

In the play-off semi-finals, Gillingham played fifth-place finishers Preston North End. In the first match of the two-legged tie, David Eyres put Preston ahead in the 54th minute. Taylor equalised with 11 minutes remaining and the match ended 1–1.^[48] The second leg was held three days later at Priestfield. Gillingham took the lead through Hessenthaler less than two minutes into the match.^[49] Having been largely thwarted by the Gillingham defence in the open 45 minutes, Preston had more goalscoring chances in the second half; goalkeeper Vince Bartram dived full-length across his goal to keep out a shot from Jon Macken. The match ended 1–0 and Gillingham progressed to the final with a 2–1 aggregate victory.^[49]

In the final Gillingham played Manchester City, who had defeated Wigan Athletic in the other semi-final. It was the first time Gillingham had played at Wembley Stadium, England's national stadium, in the club's history.^[50] The match was scoreless until the 81st minute, when Asaba gave Gillingham the lead. Taylor added a second goal five minutes later. Kevin Horlock scored for City in the 90th minute to halve the deficit and, in the fifth minute of injury time, Paul Dickov scored an equaliser to make the score 2–2 and send the game into extra time. With no further goals being scored, the match was decided by a penalty shoot-out, which City won 3–1 to gain promotion.^[51][52]

Match details

Key

FA Cup

As a Second Division team, Gillingham entered the 1998–99 FA Cup in the first round and were drawn to play fellow Second Division team Oldham Athletic. Gillingham lost 2–0 and were thus eliminated from the competition.^[54]

Football League Cup

As a Second Division team, Gillingham entered the 1998–99 Football League Cup in the first round and were paired with Southend United of the Third Division. Gillingham lost both legs of the tie 1–0.^[55]

Football League Trophy

In the first round of the 1998–99 Football League Trophy, a competition for Second and Third Division teams, Gillingham played Colchester United. Goals from Asaba, Pennock and Paul Smith and two from Taylor resulted in a 5–1 victory. In the second round, Gillingham defeated Swansea City 1–0 and then beat Torquay United by the same score in the third round. This secured the team a place in the semi-final of the southern section of the competition; their opponents were Millwall. In front of a crowd of 11,555 at Millwall's The New Den, Gillingham lost 1–0 and were eliminated from the competition.^[56]