The 1998-2002 period proved to be miserable years for Portsmouth as they were stuck near the relegation zone through out. The 1998-99 campaign saw Pompey struggle to a disappointing 21st position, fortunate to avoid relegation as they only won eleven of their matches and were defeated on 21 occasions in the league. Portsmouth’s star player, proved to be Steve Claridge, many even believed he was the sole reason behind the clubs survival of the 98-99 season.
The 99-2000 campaign witnessed little improvement in the performances, they struggled through out and finished off the season in a dismal 18th place. Once again, winning few matches, only recording 13 wins from a possible 46 matches.
The 2000-01 season saw expectations rising, Portsmouth strengthened their squad in all aspects, including the purchase of Shaun Derry from Notts County, a hard tackling defender, who arrived in to provide discipline to the Pompey defence. Despite having a decent back line, only conceding 59 goals during the campaign, Pompey found it difficult to score goals, at the end of the season they had only scored 46 league goals, the second lowest of the season. Portsmouth finished the season off in poor form as they were condemned to finishing in a dismal 20th position.
The 2001-02 season saw a slight improvement in their performances, they improved their league finish by three positions, into 17th place and quality was beginning to emerge from all areas of the field.