1998-99: Shane Westley is appointed as manager on a full-time basis and record season ticket sales are announced as the Imps prepare for life in Division Two. City find it tough going on the pitch as well as off it though with Chairman John Reames putting the club up for sale stating that, without further investment, the club would "wither and decline." Supporters group 'IMPetus' is formed with one of the targets being to raise the £25,000 that would see an elected member join the Club's Board of Directors. With the Imps rock bottom of the table, Westley is sacked and Reames installs himself as chairman/manager. Despite a slight improvement in results, a final day defeat at home to Wycombe condemns the Imps to relegation.

1999-2000: A year after putting the Club up for sale, Chairman John Reames reveals that a "substantial" investment is needed or the club may be forced to call in the administrators. The Club and Lincoln City Council finalise a £175,000 deal which sees the freehold interest in the Sincil Bank ground go back to the Football Club in a move that will enable the Imps to avoid going into administration. On the field and a season of mediocrity sees Reames hand over the managerial reins to Phil Stant.

2000-01: Rob Bradley, Chairman of the Lincoln City Membership Scheme (formerly IMPetus) is elected to the Club's Board of Directors as the supporters' representative. With the club once again struggling at the wrong end of the table, attentions turn to off-field matters as, in November 2000, John Reames, Chairman for 15 years, resigns leaving his entire shareholding of 815,821 50p shares in trust for the benefit of future investors and the Football Club. Supporter/Director Rob Bradley is named as Acting Chairman. On the field and long-serving defender Grant Brown becomes the club's all-time record appearance holder by making his 425th career appearance. "Lincoln City Football Club is now a community club, owned and run by its supporters. This is an historic day for the club and a significant day for football in general" - that was the message on February 23rd from new club chairman Rob Bradley as he announced that the Lincoln City Membership Scheme's Community Ownership Package for the shareholding of the Club was successful. Four days later and with the team languishing at the wrong end of the table, the new Board of Directors terminate the contracts of manager Phil Stant and his assistant George Foster. Former Grimsby Town boss Alan Buckley is appointed as the new manager. An upturn in fortunes sees the club finish in 18th position.

2001-02: Former manager Keith Alexander returns to Sincil Bank as assistant to Alan Buckley. Grant Brown breaks Tony Emery's long-standing Football League appearance record by playing his 403rd League game for the club. The Board of Directors announce that the collapse of ITV Digital - a new television sport channel launched amid a blaze of publicity at the beginning of the season and the subsequent loss of approximately £150,000 worth of TV revenue means that the existence of Lincoln City Football Club is very much in jeopardy. This is brought to the fore in April 2002 when the Board of Directors announce that, following advice from outside accountants and solicitors, they will be submitting a petition to the High Court for the Club to go into administration. Chairman Rob Bradley spells out the gravity of the situation by saying that the final home League game of the season against Rochdale "could be the last game in the club's history." Supporters dig deep and raise over £12,000 on the day of the Rochdale match as a "Save The Imps" campaign gets underway.

2002: A "Name Your Seat" initiative is launched, along with a host of other fundraising events, aimed at raising significant funds ahead of a High Court appearance. A week before this court appearance, the club parts company with manager Alan Buckley. On the same day that the club's petition to go into administration is successful, Keith Alexander is appointed manager. The club's creditors and shareholders accept a Company Voluntary Arrangement which guarantees that the club's future will be secure for the next two years. Five days before the new season gets underway, the Board of Directors announce that the Club is officially out of administration. Chairman Rob Bradley pays tribute to an "absolutely fantastic public response".

2002-03: With a host of new signings - the majority joining the club from non-League football - City start the season as favourites for relegation but a series of battling performances see them go into the New Year in a comfortable mid-table position. But just six defeats in the latter half of the season sees the club confound their critics and a final day draw at home to Torquay United, the equaliser coming just four minutes from time from one of the summer signings from non-League - Simon Yeo - earns the Imps a place in the Division Three Play-Offs for the first time in their history. A 6-3 aggregate success over near neighbours Scunthorpe United in the semi-finals books a place at the Millennium Stadium for the Final against AFC Bournemouth. A 5-2 reverse in the final though brings an end to the promotion dream.

2003-04 After a slow start to the season, results start to pick up when, with City lying seventh in the table, manager Keith Alexander underwent complex brain surgery at the Royal Hallamshire Hospital to repair a ruptured cerebral aneurism which had been the cause of a collapse at his home. Three months after surgery, he was back in the managerial hot seat alongside assistant Gary Simpson who had taken over his duties in his absence, and his first game back in the dug-out was the Imps' local derby against Boston United on February 7th, with the Imps still seventh in the table. City spent the remainder of the season either in or on the fringes of the play-off places and with the average home League attendance of 4,911 being a 66% increase on the 2001/02 figure, the Imps once again found themselves in the end-of-season play-offs, despite picking up just one win from their last five matches. A second successive trip to the Millennium Stadium is thwarted though as City lose out to Huddersfield Town in the semi-finals 4-3 on aggregate.

2004-05 Once again, City started the season slowly, although striker Gary Taylor-Fletcher equalled a 106-year record by scoring in the first six matches, but a good run of form prior to Christmas saw the Imps move up into the top five places with manager Keith Alexander winning the League's "Manager of the Month" award for November. City maintained their place at the top end of the table and a sixth-placed finish saw them reach the play-offs for the third successive season. A 2-1 semi-final aggregate victory over Macclesfield Town saw them return to the Millennium Stadium but promotion once again proved to be elusive as Southend United came away 2-0 winners after extra-time. Promotion would have been the perfect send-off to Supporter Director Rob Bradley who, after four years in the Chairman's seat, decided to step down at the end of the season. Gareth McAuley, a pre-season signing from Coleraine, becomes the first Lincoln player to represent one of the home countries at full international level for almost 22 years when he appears as a second half substitute for Northern Ireland in a friendly against Germany at Windsor Park.