1986

Joins Milan’s youth team as a 10-year-old, and goes on to spend seven years with them.


1987/88

Wins his first ever Scudetto with Milan on the last day of the season, edging out an impressive Napoli outfit by three points.


1988

March 31 – Makes his debut for Italy in a friendly against Yugoslavia that ended 1-1.


1988

June 10-22 – Plays all four matches at EURO 1988 in his first major international tournament.


1989

May 24 – Wins his first ever European Cup, as Milan smash four past Steaua Bucharest to win their third ever title.


1990

May 23 – A second consecutive European Cup for Maldini and his team-mates, as they edge Benfica 1-0.


1990

June-July – Participates in his first World Cup in Italy, only to be eliminated in the semi-final on penalties by Argentina.


1991/92

His Milan side win their 12th Scudetto, in an unbeaten season.


1992/93

Wins his third Scudetto with the Rossoneri, in a season where the champions finished four points clear of their cross town rivals Inter.


1993

January 20 – Scores his first international goal for Italy in a friendly against Mexico (2-0), exactly eight years after making his league debut.


1993/94

Celebrates his third consecutive Scudetto with Milan, despite his side managing to score only 36 goals in 34 games.


1994

May 18 – Milan continue their dominance in Europe, as they claim their first ‘Champions League’ crown by thrashing Barcelona 4-0.


1994

June-July – Captains his country for the first time at a major tournament, at the World Cup in the USA. His side go on to lose the final against Brazil on penalties, with Roberto Baggio missing the last kick.


1995/96

Milan celebrate their fourth Scudetto in five seasons, with several dominant performances, including a 7-1 demolition of Cremonese.


1998/99

Maldini’s sixth domestic championship of his career, as the Rossoneri leave it until the very last day to clinch the title over Lazio.


1999

June 5 – Scores his seventh and last ever goal for Italy in Bologna against Wales in a EURO qualifier.


2000

July 2 – Italy narrowly lose the final of EURO 2000 to France after being defeated by a David Trezeguet golden goal. It would be the closest Maldini would ever come to winning a significant international tournament.


2000

October 7 – Breaks Dino Zoff’s Italian record for international appearances after his 113th match in a World Cup qualifier against Romania.


2002

June 18 – Makes his final appearance for the Azzurri, as the Italians are controversially eliminated by South Korea at the 2002 World Cup.


2003

May 28 – The Rossoneri claim their sixth Champions League triumph, following a victory on penalties against Juventus at Old Trafford.


2003

May 31 – Milan win their only Coppa Italia in Maldini’s time at the club, defeating Roma 6-3 on aggregate, following a 2-2 draw in the second leg.


2003/04

This would be Maldini’s seventh and final Serie A title, after his side cruised to their 17th championship, seeing off the second placed Roma by 11 points.


2005

May 25 – Despite scoring the fastest ever goal in a European Clubs’ Cup final after just 51 seconds, Maldini labels his side’s failure to win the Champions League against Liverpool as the "worst moment of his career".


2005

September 25 – This time he breaks Dino Zoff’s Serie A appearance record after playing his 571st match against Treviso.


2007

May 13 – Becomes the first player to make 600 appearances in Serie A, in a 1-1 draw away to Catania.


2007

May 23 – His side’s seventh Champions League would go on to be his final major success in European football, as Milan avenge their disastrous defeat to Liverpool two years prior, with a 2-1 victory over the Reds in Greece.


2007

December 16 – Announces his decision to retire from football at the end of the 2007-08 season, following Milan’s 4-2 triumph in the Club World Cup final against Boca Juniors.


2008

February 16 – Makes 1000th senior appearance for Milan and Italy combined, after coming on as a substitute against Parma.


2008

March 5 – Reconsiders decision to retire at the end of the season, following Milan’s elimination from the Champions League at the hands of Arsenal.


2008

June 6 – Signs a contract extension for a further year with Milan.


2009

April 18 – Officially announces that he will retire at the end of the season, and this time there would be no going back.


2009

May 24 – Makes his final appearance for the Rossoneri at San Siro, as Milan go down in a thrilling match against Roma 3-2.


2009

May 31 – Paolo Maldini played his last match as a professional footballer, against Fiorentina at the Artemio Franchi stadium.