The 1999–2000 season was the 102nd season of competitive football played by Arsenal. The club ended the campaign second in the league, 18 points behind Manchester United. Arsenal exited both domestic cup competitions on penalties, being eliminated by Leicester City in a FA Cup fourth round replay and by Middlesbrough at the same stage of the Football League Cup. For the second consecutive season Arsenal failed to progress past the group stage of the UEFA Champions League; a third-place finish however earnt them a consolation place in the UEFA Cup. Arsenal eventually reached the final to play Galatasaray in Copenhagen – the match was overshadowed by altercations between both sets of supporters. The team lost 4–1 on penalties after a goalless draw.

A number of signings were made by Arsenal in the summer transfer window, namely defenders Sylvinho and Oleg Luzhny, and striker Thierry Henry, who joined from Juventus on a club record fee. Davor Šuker departed Real Madrid to sign for Arsenal, following Nicolas Anelka's move in the opposite direction. Steve Bould left Arsenal to play for Sunderland, while Stephen Hughes signed for Everton in the spring.

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