Upon joining the league, New Brompton turned professional, with the players agreeing to be paid 12 shillings per match, and promptly won the Division Two championship in the 1894–95 season.
[7] New Brompton struggled in Division One, generally finishing close to the foot of the table, but did reach the first round proper of the FA Cup for the first time in 1899–1900, losing 1–0 to Southampton.
In the same season the club was forced to play a league fixture at the home ground of Woolwich Arsenal when Priestfield was closed due to crowd trouble in a match against Millwall.
[8] In the 1907–08 season, under the management of the former England international Stephen Smith,[9] New Brompton finished bottom of the table,[10] avoiding relegation only due to the expansion of the league, but did achieve a cup victory over First Division Sunderland, remembered for a hat-trick from Charlie McGibbon.
[12] The side again finished bottom of the division in the 1914–15 season, but avoided relegation for a second time when the league was suspended due to the escalation of the First World War.
Once the competition resumed after the war Gillingham, once again wearing black and white,[13] continued to fare poorly, again finishing bottom of Division One in the 1919–20 season.
Striker Hughie Russell scored nine goals in the match, and missed out on double figures when he hit the bar late in the game.
[31] Gillingham applied for re-election to the Football League in the summer of 1948 but, despite producing a glossy brochure detailing the team's achievements, the club saw its application rejected, with only one vote cast in its favour.
[32] Gillingham's first game back in the Football League saw the Kent club hold fellow new entrants Colchester United to a 0–0 draw at Priestfield in front of 19,542 fans.
[42] After guiding the club to promotion Andy Nelson left to take over as manager of Charlton Athletic[43] and was replaced by Len Ashurst, but his managerial reign lasted only 16 months.
[45] Peacock put together a team which developed a reputation for exciting, attacking play,[46] and also brought through the ranks a number of young players who went on to achieve success at a higher level, including Micky Adams,[47] Steve Bruce,[48] and Tony Cascarino, who was famously bought from non-league Crockenhill in exchange for a set of tracksuits.
[16] The club's failure to gain promotion meant that it was unable to hang on to the ambitious Cascarino,[50] who was sold to Millwall for £225,000, but despite the loss of the team's star striker the Gills' 1987–88 season began with a flurry of goals.
On consecutive Saturdays Gillingham beat Southend United 8–1 and Chesterfield 10–0 (the latter a new club record for a professional match), but the early-season promise faded and in December Peacock was controversially sacked after a 6–0 defeat to Aldershot.
[37] Former Gillingham player Damien Richardson became the club's next manager, with veteran goalkeeper Ron Hillyard as his assistant, but the club's financial situation was poor and the pair struggled to produce results with a squad composed of ageing journeymen and untried youngsters, and both men were sacked in September 1992,[52] with Glenn Roeder taking over as manager.
[37] Nonetheless, the financial crisis continued at Priestfield, and steadily improving league form over the next two seasons did little to disguise the fact that the club was in real danger of going out of existence.
[54] The club eventually went into receivership in January 1995,[55] and by the end of the 1994–95 season, with Gillingham facing the threat of being expelled from the Football League and closed down, fans were wondering whether they had seen the last ever Gills match.
[54] Scally brought in new manager Tony Pulis, who signed almost a complete new team and led Gillingham to promotion in his first season, finishing second in Division Three (now Football League Two).
Following goals by the prolific partnership of Robert Taylor and Carl Asaba, the Gills led 2–0 with less than two minutes left, only to see Manchester City score twice, the equaliser in injury time, and then win a penalty shoot-out 3–1.
In the 1999–00 season Gillingham went on a club record breaking FA Cup run, beating then-Premiership teams Bradford City and Sheffield Wednesday before losing 5–0 to Chelsea in the quarter-finals.
Former team captain Andy Hessenthaler was appointed player-manager, having previously served as player-coach,[59] and led the club to league finishes of 13th, 12th and 11th in his first three seasons in charge.
[61] Gillingham then appointed former Burnley boss Stan Ternent as manager,[62] but despite a late run of positive results, he could not prevent the Gills' relegation to League One on the last day of the season.
[72] The following season the Gills earned promotion through the play-offs after finishing fifth in the league, Simeon Jackson scoring the only goal in the final against Shrewsbury Town at Wembley Stadium.
[76] For two consecutive seasons the Gills finished just outside the play-off places in League Two,[16] following which Hessenthaler was moved to the position of Director of Football and Martin Allen appointed as manager.