The 1999–2000 season was Arsenal Football Club's eighth season in the Premier League and their 74th consecutive season in the top flight of English football. 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, earned 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. Arsenal lost 4–1 on penalties after a goalless draw.

Sylvio Mendes Campos Júnior, commonly known as Sylvinho, is a Brazilian football manager and former player, currently coaching the Albania national football team.