1968: Born June 26 in Milan, Italy.
1985: Makes league debut at the age of 16 for AC Milan as a half-time substitute for the injured Sergio Battistini against Udinese. It was Maldini's only league appearance of the campaign, but the teenager was the Rossoneri's first-choice left-back the following season.
1986: Maldini, the son of Cesare Maldini, was called up by his father to the Italy Under-21 squad. He earned 12 caps and scored five goals in two years.
1988: At the age of 19, Maldini made his full international debut in a 1-1 friendly draw with Yugoslavia on March 13. Made one appearance for the Azzurri at the 1988 Summer Olympics. He also claimed the first of his seven Scudetto titles in the 1987/88 season before starring in all four of Italy's games at the 1988 European Championships.
1989: Helps Milan win European Cup with 4-0 rout of Steaua Bucharest in final. Also wins UEFA Super Cup.
1990: May 23 - Helps Milan retain European Cup with 1-0 win in final over Benfica. Also retains UEFA Super Cup.
1990: Features in his first World Cup where hosts Italy progress to the semi-final before succumbing to Argentina on penalties.
1992: Wins Serie A title and Italian Supercoppa.
1993: Retains Serie A crown and Supercoppa. Scores first international goal in his 44th cap in a 2-0 friendly win over Mexico on January 20.
1994: Milan go on to complete hat-trick of Serie A titles and Supercoppas. Wins Champions League, beating Barcelona 4-0 in final. Captains Italy in World Cup in USA. Italy lost to Brazil in the final on penalties. Named in the team of the tournament 32 years after his father received the same honour at the 1962 World Cup.
1996: Helps Milan regain Serie A title but helpless to prevent Italy from exiting Euro 96 at the group stage.
1998: Plays key role as Italy reach quarter-finals of the World Cup in France.
1999: Wins Serie A crown.
2000: Helps Italy reach the final of Euro 2000 in which they lose to France.
2002: Retires from international football after Italy's elimination from the World Cup in the last 16. He represented his country 126 times and scored seven goals, all coming in home games. Maldini, the most capped player ever for Italy, wore the captain's armband a record 74 times.
2003: Wins Coppa Italia. Wins Champions League, beating Juventus on penalties after goalless draw after extra time in Manchester.
2004: Wins Serie A title and Supercoppa.
2005: May - Scores the fastest goal in Champions League final history after just 51 seconds of Milan's clash with Liverpool. Also becomes the oldest player ever to score in a final at 36. Liverpool fought back from 3-0 down to win on penalties.
2007: Announces he will retire at the end of the 2007/08 season. Captains Milan to Champions League glory, beating Liverpool 2-1 in Athens final. Also wins FIFA Club World Cup.
2008: February - Reaches 1,000 senior games with Milan and Italy when brought on as a substitute against Parma.
March - Decides he will delay his retirement for a further year.
May - Plays his 600th Serie A match in Milan's 1-1 draw at Catania.
2009: May 24 - His final appearance at the San Siro.
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