The nineties began with a new manager, a legend to be in fact as Cyril Knowles, a distinguished international full back, came to the north-eastern club after relative success at Darlington and Torquay where he picked a trophy up at each. Bringing in a number of new players he managed to turn what was looking to be a dire season around and lead the club to a safe 19th, gaining them 55 points after they had 9 from 19 games. the next season things got better for club as the firing front pair of Paul Baker and Joe Allon sent Hartlepool towards the play off places till disaster struck and the legend that is Cyril Knowles was diagnosed with a brain tumour and had to step down, sadly passing away in the summer of 1991.
Following in these footsteps was going to be a tough ask and was something that Alan Murray did as, for the second season in a row Hartlepool where contenders for promotion thanks again to Joe Allon and Paul Baker, securing the promotion on the final day of the season with a 3-1 victory over Northampton. the front pair were becoming more than prolific for the club as Allon secured over 30 goals for the season and Baker, along with Paul Dalton also managed double figures. the first season of division three saw them finish a very respectable 11th as they coped with the loss of Joe Allon to Chelsea by bringing in Andy Saville and Lenny Johnrose that season, and then Dean Emerson, Ryan Cross and John Gallagher the following summer as they looked to assert themselves on the league. This worked as by October they were level on points in the re-formatted division two with leaders West Bromwich Albion. This season was to become a very good season for the seaside club as they were still in with a chance of play off promotion at the start of 1992, but little did the fans see what was about to arise. Following an astonishing win over Crystal Palace, a premier league side, in the FA Cup, it became known to the public that the club were having many financial difficulties and it resulted in the release or sale of many of their top players. in conjunction with this they also set a record nobody would want, going 1227 minutes without scoring a goal. they slipped down the league to 16th, Murray was sacked, and Viv Busby came in to the job, even if he did last till November.
John McPhail came into the position but could do little to stop the slide down the league as they were thrashed 8-1 at home on the final day of the season. It all began a long line of events for the next five seasons. It truly was a rollercoaster ride for the club as they can a revolving door of managers, but on the bright side were financially stable as the club was sold to local businessman Harold Hornsey. Even with the financial stability, there was still little money available to bring players in and the team was struggling as McPhil was replaced by Dave McCreery, and even he didn’t last long as Keith Houchen, a former player, came back to the club at the end of the 1994-95 season. Lasting 18 months, he was replaced by Mick Tait. these off-the-field turbulences took there toll on the team as a whole s during this period they failed to reach higher than 18th, finishing 20th on two occasions. There was also a second change of ownership within the decade as Hornsey sold the club to oil firm IOR, bringing in current chairman Ken Hodcroft in that position.
Tait still had a rough time of it after the change in ownership as they struggled throughout the 1998-99 season, when even the signing of former England striker Peter Beardsley couldn’t help the club; he was sacked 1999. This was a time for Hartlepool United when they were going to start moving up as new manager Chris Turner was able to help them beat the drop despite being four points adrift at the bottom of the table at Easter.
The next 3 seasons all saw them reach the semi-finals of the play-offs and all saw them get knocked out at that stage too, once to local and bitter rivals Darlington. Then came promotion as they finished 2nd in the league, despite the rotating door of managers striking again as Chris Turner left for Sheffield Wednesday during the season and then his replacement, Mike Newell, being replaced by Neale Cooper in that summer. This time however, the success was to continue despite these distractions, as Neale Cooper was able to guide them to the second division playoffs in their first year, a season that saw them record an 8-1 victory over Grimsby. It also became the season for a younger legend as Eifion Williams was to become only the second player to get an international call-up while playing for the club, as Wales came knocking. For the 5th time in 6 seasons, Hartlepool were to reach the play-offs, and this time reach the final as they beat Tranmere Rovers 6-5 on penalties, but lost 4-2 to Sheffield Wednesday in the final. Neale Cooper was also another loss in the 2005-06 season, but his assistant was to take over, Martin Scott. the again, after a fight with a player and more off the field turbulences he was sacked and to be replaced by youth team coach Paul Stephenson, their 5th manager in 6 years.
The club was relegated and Danny Wilson took over on a more permanent basis, which saw more good fortunes come to the club as they set a football league record of most consecutive wins without conceding a goal, even if this was beat later in the season by Stockport County. the team went on to have a 23-game unbeaten streak and bounced straight back into League one as it was now called, and have since had stability and stayed in League one. however, in late 2008 Danny Wilson left the club after a poor stretch of results and it was left to Chris Turner to take temporary charge.