In the knockout stage, United played two Italian sides in the quarter- and semi-finals; Internazionale and Juventus respectively. Prior to 1999, United had never won on an Italian pitch.

In the quarter-final, David Beckham was playing against Diego Simeone for the first time since the 1998 World Cup. In the first leg at Old Trafford, United beat Inter 2–0 with two almost identical goals from Yorke, both from crosses by Beckham, while Simeone's second half goal was disallowed for pushing. In the San Siro, Paul Scholes scored a late, away goal to level the game at 1–1. United advanced 3–1 on aggregate but still hadn't won in Italy.

Manchester United [2 - 0] Inter Milan

Manchester United [1 - 0] Inter Milan, Yorke

Manchester United [2 - 0] Inter Milan, Yorke

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