Maldini made his league debut on
January 20, 1985, at the age of sixteen, against
Udinese Calcio as a halftime substitution for
Sergio Battistini. It would be his only league appearance of the campaign, but he was in the starting eleven the
following season.
The
1987–88 Scudetto marked Maldini's first major trophy, and the first of seven league titles, with the club. He was also part of AC Milan's undefeated "Dream Team" from the late 1980s to the early 1990s.
In addition to winning his third
Champions League and reaching the
1994 FIFA World Cup final, Maldini became the first defender ever to win
World Soccer magazine's annual
World Player of the Year Award. During his acceptance speech, Maldini called his milestone
"a particular matter of pride because defenders generally receive so much less attention from fans and the media than goalscorers. We are more in the engine room rather than taking the glory." He then singled out Milan captain
Franco Baresi as a player who
"really [deserved] to receive the sort of award I have received."
Maldini played his 600th Serie A match (not including playoff matches) on
May 13, 2007, in a 1-1 draw at
Calcio Catania. On
September 25, 2005, Maldini broke
Dino Zoff's Serie A appearance record after playing his 571st league match against
Treviso F.B.C.; seven days earlier, he had played his 800th game in all competitions for Milan.
Maldini has participated in eight
UEFA Champions League finals during the course of his career, which is more than any other active player and near by one to a record held by
Francisco Gento. He has lifted the championship trophy five times, the latest coming in Milan's 2-1 victory over
Liverpool F.C. in the
2007 CL final on May 23. In an interview with
ESPN that aired prior to the broadcast of the 2007 final, he labeled the
2005 final, which Milan lost on penalties to Liverpool in extra time after blowing a 3-0 lead, the worst moment of his career, even though he had scored the fastest-ever goal in a European Clubs' Cup final just 51 seconds into the match, in the process also becoming the oldest player ever to score in a final.
In November 2005, he announced his plans to retire at the end of the 2006-07 season, but relented and decided to stay on for one more year, making his impending retirement effective at the end of the '07-08 campaign. Milan plan to retire his number 3 shirt, but it will be bequeathed to one of his sons if he makes the club's senior side. His eldest son, Christian, is 12 years old and is currently playing for the Milan youth squad.
