Gianluca Vialli was installed as the new manager at Chelsea for the 1998 – 1999 season, replacing Ruud Gullit at the club. Vialli also played for the side in his forward role during the campaign and the response was immediate, they enjoyed an incredible league season as they finished it off in third position, earning them a Champions League birth. The Blues reached the quarter finals of the League cup; however they narrowly lost 2-1 against Wimbledon. The Chelsea goal keeper, Ed De Goey was in outstanding form for the club as he only conceded 30 goal through out the campaign, fewer than any other keeper. Brian Laudrup, Marcel Desailly and Pier Luigi Casiraghi all made their debut for the Blues during the 98 – 99 season.
The Blues enjoyed another fine campaign as they finished the season off in an impressive fifth position. The enjoyed another incredible FA Cup run as they reached the final of the domestic cup competition, meeting Aston Villa in the final at Wembley. The Blues defeated the Midland’s club, 1-0, and it was their FA cup hero of three years ago, Roberto Di Matteo who scored the winning goal for the Blues. Tore Andre Flo, Gianfranco Zola, Gustavo Poyet and Dennis Wise were all in fine form for the Blues.
The 2000 -01 season proved to be a mixed bag, they enjoyed a fairly decent league season as they finished it off in a respectable sixth place. Jody Morris and John terry both made impressive performances for Chelsea during the league campaign.
The Blues looked in search of success during the 2001 – 2002 season and managed another sixth place finish in the premiership. They enjoyed fantastic cup runs; however a 5-1 defeat in the semi final of the League cup was not on the agenda. They reached their second FA cup final in three years as they met Arsenal in the final. The Gunner managed to defeat the Blues 2-0 in a match at the Millennium Stadium. Recent signing, Frank Lampard was in fine form for the blues. The major blip of their campaign was their performance in the UEFA Cup as they crashed out early suffering defeat against Israeli football club, Hapoel Tel Aviv.