Manager Gianluca Vialli added Didier Deschamps from Juventus, Chris Sutton from Blackburn Rovers, and Mario Melchiot from Ajax as Chelsea strengthened in preparation for the club's participation in the 1999-2000 UEFA Champions League. Deschamps becoming the third member of France's FIFA World Cup winning team at Stamford Bridge, joining Frank Leboeuf and Marcel Desailly.
What a season. Chelsea finished 5th in the FA Premier League, making headlines away at Southampton by fielding the first ever English team to play an English league game without any Englishman in the starting lineup. In early January George Weah joined on loan from AC Milan and scored the only goal of the game versus Tottenham Hotspur the very next evening. The FA Cup was won again. In the last final at the old Wembley Stadium, Roberto Di Matteo scored in extra-time to secure a 1-0 victory versus Aston Villa. Gianluca Vialli's 4th trophy as Player-Manager/ Manager. Captain Dennis Wise was Chelsea Player of the Year.
In The UEFA Champions League, Chelsea progressed past Skonto FC in the third Qualifying Round to qualify for the UEFA Champions League First Group Stage where, with Dennis Wise memorably scoring in the San Siro, Chelsea and Hertha Berlin qualified at the expense of Galatasaray and AC Milan.
In the Second Group Stage both Lazio and Chelsea progressed at the expense Feyenoord and Olympique de Marseille, leading to Chelsea being drawn against Barcelona in the Quarter-Final.
In a dramatic UEFA Champions League Quarter-Final 1st-Leg at Stamford Bridge, Chelsea blitzed Barça with 3 first-half goals in quick succession as a Gianfranco Zola inch perfect 20 yard free-kick was quickly followed by 2 Tore André Flo goals to put Chelsea 3-0 in front. Barcelona secured a vitally important away goal in the 64th minute when Luis Figo converted from a Rivaldo cross at The Shed End. The Figo goal was pivotal. Barcelona squared the tie in the 2nd-Leg with a 3-1 win in 90 minutes in Camp Nou before clinching the victory in extra-time, ultimately winning 5-1 on the night and 6-4 on aggregate. The Chelsea v Barcelona UEFA Champions League rivalry was up and running.
SCORE DRAW Official Retro Shirt Match:
Chelsea 3 v 1 Barcelona.
Wednesday 5 April 2000.
UEFA Champions League Quarter-Final 1st-Leg.
Chelsea Team: Ed De Goey. Albert Ferrer. Celestine Babayaro. Marcel Desailly. Emerson Thome. Dan Petrescu (Roberto Di Matteo). Didier Deschamps. Dennis Wise. Jody Morris. Tore André Flo (Chris Sutton). Gianfranco Zola.