After a very good third-place finish last season, Chelsea were expected to go one better and win the title. France captain Didier Deschamps was signed for £3 million from Juventus to add even more quality and experience to a Chelsea midfield that already boasted Dennis Wise, Roberto Di Matteo and Gustavo Poyet. Blackburn Rovers striker Chris Sutton was also signed for £10 million, but he proved to be a flop with only one league goal all season. His strike partner, Gianfranco Zola, had a poor league season by his standard, scoring just four goals, but he made up for that by again setting up many more goals for the team. In contrast to his average league form, Zola made Europe sit up and notice as he led Chelsea's Champions league campaign, scoring a spectacular free kick in a 3–1 win over F.C. Barcelona at Stamford Bridge, but Chelsea were eliminated in the second leg at the Nou Camp. On the Premiership front, Gianluca Vialli's side finished a solid fifth place in the final table but were too inconsistent to mount anything like a title challenge. Chelsea won their fourth cup in four seasons with a 1–0 win over Aston Villa at Wembley, giving them the last cup final triumph at the old Wembley stadium before it was rebuilt.

Source: 1999-2000 FA Premier League table

Source: 11v11.com: 1999-2000 Chelsea results
Ground: A = Away; H = Home. Result: D = Draw; L = Loss; W = Win; P = Postponed.

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