The 1999–2000 season was Manchester United's eighth season in the Premier League, and their 25th consecutive season in the top division of English football. United won the Premier League title for the sixth time in eight seasons (with a record 18-point margin and 97 goals scored) as well as becoming the first British club to win the Intercontiental Cup when they defeated Palmeiras 1-0 in Tokyo. However, they surrendered their European Cup title with a 3–2 defeat by eventual champions Real Madrid in the quarter-finals. The club controversially did not defend their FA Cup crown, upon request by The Football Association, to compete in the inaugural FIFA Club World Championship in Brazil instead.

Mark Bosnich, previously at United as a reserve goalkeeper from 1989 to 1991, returned to the club as Peter Schmeichel's successor, but failed to live up to expectations and in September, the club swooped for Italian Massimo Taibi to provide competition for him. However, Taibi suffered some high-profile mistakes and returned to his homeland at the end of the season after just five games for the club. United then solved the goalkeeping crisis by paying AS Monaco £7.8 million for Fabien Barthez. Also new to the squad for 1999–2000 were French defender Mikaël Silvestre and South African winger Quinton Fortune. Jesper Blomqvist and Wes Brown missed the entire season due to injury, while similar misfortune restricted defenders David May and Ronny Johnsen to three first-team appearances between them. Jordi Cruyff left the club on a free transfer to Deportivo Alavés at the end of the season, seeing out his four-year contract at a club where he had failed to claim a regular first-team place.

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