David Webb started the 1990/91 with a much changed squad in spite of a successful promotion campaign. Top scorer for the previous three seasons, David Crown was allowed to leave for Gillingham and in his place came Brett Angell, a £100,000 capture from Stockport County. Other significant arrivals included Chris Powell and John Cornwall.
The season started very well indeed with eight wins in the opening nine matches ensuring the Blues lead the table in the early weeks. Less impressive though was an 8-0 trashing at Crystal Palace in the Rumbelows Cup. The unpopular Leyland DAF Cup however saw the Shrimpers find their scoring boots with a club record equalling 10-1 victory against Aldershot in the opening. New man Angell claimed four and there was also a hat-trick for Steve Tilson. A subsequent tie against Torquay saw the Blues rattle in seven goals without reply in the final 25 minutes of the game, Andy Ansah this time keeping the match ball.
League form dipped in the Christmas and New Year period and Webb strengthened his defensive options with Pat Scully arriving from Arsenal. As the run in to the end of the season began missed opportunities at home to the likes of Chester, Wigan and Cambridge saw promotion rivals gain valuable ground. A win at Exeter though saw Blues in the home straight knowing a win on the road again up at Bury would secure back to back promotions for Webb’s men. A tense encounter ensued at Gigg Lane, not helped by Scully’s early dismissal for an injudicious challenge. The ten men rallied and as the game entered the closing stages Andy Ansah yet again rampaged down the right flank, his scuffed cross fell to Ian Benjamin. The man who had terrorised Southend in the 80’s as part of the powerful Northampton side turned neatly on the edge of the box. His deft shot found the corner of the home net and the away terrace paused momentarily to let the realisation dawn, and then unbridled jubilation was unleashed. It was a truly iconic moment in the club’s history.
Southend had won promotion to the second tier of English football for the first time ever. The squad was bolstered with the arrival of Kevin O’Callaghan and Andy Sussex. After a difficult start goals started flowing, Brett Angell set a post-War club record by scoring in seven consecutive games, falling just one short of Billy Hick’s all time record. For the first time in the club’s history the team entered the FA Cup at the third round stage, drawing Everton away at Goodison Park. Blues gave a great account of themselves losing to a single Peter Beardsley goal. The match had come three days after a 4-0 home win over Newcastle United on New Years Day which had seen the Shrimpers temporarily top the First Division table.
Form wavered though and despite a club record fee of £175,000 spent on the services of Keith Jones, the club finished in twelfth position in the final analysis.
The season finished on a flat note when David Webb resigned for a second time. The board appointed the experienced Colin Murphy as his replacement and his unusual training methods and rambling philosophical programme notes had the Blues faithful scratching their heads. On November 21st however, Murphy pulled off a master stroke by rescuing a young centre forward from Crystal Palace reserves. Stan Collymore burst onto the Southend scene like no other player in living memory. Raw strength, skill and energy saw him rattle in 18 goals in 33 games. It had, however, remained a season of struggle and Murphy paid the price with his job. Barry Fry was drafted in to save the Blues from the drop. He seemed to get even more out of Collymore and four wins out of the last four home games ensured survival on the last day of the season against Luton Town. Collymore was chaired of the pitch in his underpants, it was to prove to be the last time he wore and lost a Southend shirt.
In the summer he was sold to Nottingham Forest for a fee of £2,250,000, shattering the club’s record fee. With Fry’s undoubted acumen in the transfer market, the fee eventually climbed to an astonishing £3.57 million. It was widely viewed that Collymore was the most naturally gifted player the club had ever fielded.
Fry shed many players in the summer and bought in the likes of Ricky Otto, who would light up Roots Hall with his mesmeric dribbling, Jason Lee and Gary Poole who would cost a club record fee of £400,000. A clutch of players also arrived from Fry’s former club Barnet. By January however, Fry was gone. Despite saying he wouldn’t leave the club he changed his mind and amid not inconsiderable acrimony departed for Birmingham City. Former Southend player Peter Taylor was handed the reigns and the team laboured to a final placing of 15th.
Taylor again struggled to get the team going in the 1994/95 campaign with goalscoring proving to be a real problem for his charges. Despite the luxury of the vastly experienced Ronnie Whelan in midfield, the team struggled for form and as relegation looked a serious possibility Taylor resigned in February. Steve Thompson was handed the job on a caretaker basis with a dozen games remaining. It marked an unbelievable change in the team, confidence flowed through every player and goals came thick and fast. Eight wins under Thompson ensured a comfortable placing of 13th in the final reckoning.
Thompson turned down a full time contract and Ronnie Whelan took over as player-manager, although he would suffer a career ending injury in the opening game of the 1995/96 season. The club spent unprecedented amounts in the transfer market, Mike Marsh arrived from Galatasaray for a record £500,000 whilst Mike Lapper, Andy Rammell, Mark McNally and Jeroen Boere all commanded six figure fees.
Despite the influx of new players goalscoring again proved to be the weakness in the team, Dave Regis would top score with eight League goals despite leaving the club in February. A final placing of 14th was only seven points above relegation in a tight division.
The success and glamour of the first half of the 1990’s would be mirrored in the starkest possible fashion by the second period of the decade. Whelan’s second season in charge was an unmitigated disaster with the club finishing bottom of the First Division table winning just eight games all season.
Whelan departed and ex West Ham and England defender Alvin Martin was charged with halting the slide for the 1997/98 season. It was another desperate period for the Blues, a run of five games without even being able to score a goal at the turn of the year summed up a dire campaign. The Blues were relegated for a second time in successive seasons, again finished at the foot of the table. For the 1998/99 season Martin drafted in the experienced Mick Gooding as his assistant but to no avail, an 18th place finish saw the club flirting dangerously with the trapdoor to the Conference.
The final season of the decade saw Martin Carruthers arrive from Darlington for £50,000 and he would score 19 times for the Blues in his debut campaign. However goals among the other players were scarce and by early March Alvin Martin had left the club as manager. The Blues board turned to another former Southend player as the new man in charge as Alan Little was appointed manager after a successful spell as a player more than twenty years previously. The final nine games of another wretched season mustered only five League goals as the Blues limped to 16th place in the table. However, popular left back Nathan Jones bought the curtain down on the 20th century with a wonder goal in the final game at home to Cheltenham Town.