AC Milan 2003

Coach: Carlo Ancelotti

Carlo Ancelotti's Milan won their sixth European Cup in 2003, edging out Juventus on penalties in an all-Italian final at Old Trafford after a goalless 120 minutes — Andriy Shevchenko converted the winning spot-kick. This was the squad built around Paolo Maldini and Alessandro Costacurta at the back, Gennaro Gattuso and Andrea Pirlo controlling midfield, and a mix of Rui Costa's creativity with the goals of Shevchenko, Filippo Inzaghi and a young Kaká establishing himself as a first-team regular. Along the way to the final, Milan eliminated Ajax and then their own city rivals Inter in an all-Milan semi-final decided on away goals — a fixture made even stranger by both legs technically being 'home' games at the shared San Siro. Domestically, Milan finished third in Serie A that season, well behind champions Juventus, making the European triumph feel even sweeter as validation of Ancelotti's continental-focused squad building. It was the first of three Champions League finals Milan would reach in a five-year span (2003, 2005, 2007), a run matched by almost no other club in the modern era, and it re-established Milan as Italy's dominant force in Europe after a decade in Juventus and Inter's shadow.