1968: Born July 9 in Rome.
1985: Joins home-town club Lazio, then in Serie B, but does not break into first team.
1986: Drops down a division to Ternana, playing 27 matches and scoring two goals in 1986-87.
1987: Returns to Lazio but again fails to make a first-team appearance as they win promotion to Serie A.
1988: Makes his Serie A debut for Lazio in October and plays 30 times that season, scoring one goal.
1989: Plays 24 matches, scoring three goals.
1990: Moves to Juventus and scores three times in 23 appearances.
1991: Plays 55 games over the next two seasons, hitting three goals.
1993: Heads south to Napoli, making 26 appearances and scoring five goals.
1994: Returns to Juventus but moves on to AC Milan without playing a league game.
1994: Restricted to just four starts at Milan. Makes another 11 appearances from the bench and scores one goal against Fiorentina in January.
1996: Leaves the San Siro in June to join Celtic in a £1million deal.
1996: Becomes a firm favourite with Celtic fans, scoring 12 goals in 26 league games as the club finish runners-up to Rangers in title race. In total scores 15 times in 37 matches.
July 9 - Breaches his contract by refusing to join his Celtic team-mates at their Dutch training camp and Celtic threaten him with a three-year ban.
July 15 - Announces his intention to quit Celtic after new coach Wim Jansen says he is unimpressed with the player's attitude in training.
August 6 - Joins Sheffield Wednesday in a £4.5million deal. Scores 12 times in Premiership to finish the club's top scorer.
September 26 - Pushes referee Paul Alcock to the ground after being sent off in the clash with Arsenal at Hillsborough.
October 23 - Receives 11-match ban from the Football Association, including a statutory three matches for being sent off in the previous month's game against Arsenal. He is also fined £10,000.
November 3 - Wednesday reveal they have imposed their own fine on Di Canio for his dismissal and push on Alcock, believed to be two lots of two weeks' wages, totalling £68,000.
December 12 - Wednesday suspend Di Canio for two weeks without pay when he does not return from a break in Italy. Later says he is suffering from stress and depression.
December 26 - Is suspended for a further two weeks and docked another two weeks' wages by Wednesday when he fails to appear for home game against Leicester.
1999: January 9 - Is suspended and fined another two weeks' wages by Wednesday.
January 19 - Declared fit after Wednesday receive report into his health. But Wednesday refuse to pay Di Canio the £102,000 he was fined while he was in Italy claiming he was ill.
January 27 - Joins West Ham for £1.7million.
February 9 - Charged with misconduct by FA in relation to incident during Premiership game with Villa when he appeared to make an insulting gesture. Later fined by the FA.
2001: November 29 - Awarded FIFA's Fair Play Award for 2001 in recognition of his "special act of good sportsmanship" in West Ham's game at Everton the previous season.
2002: January 6 - West Ham boss Glenn Roeder confirms Manchester United made a bid for the player which the club rejected.
2003: August 11 - Signs a one-year deal with Charlton as a free agent.
2004: Returns to former club Lazio, but his relationship with the club's Ultras generates negative headlines.
2006: Sees out his career with Cisco Roma, retiring in 2008.
2011: May - Appointed Swindon manager.
2012: April - Swindon are promoted from League Two with 93 points, having lost the Football League Trophy final against Chesterfield.
2013: February 18 - Resigns as manager citing issues with the club's hierarchy.
February 21 - Reportedly returned to the County Ground in the dead of night to remove photographs from his fruitful spell at the club.
March 31 - Named as Sunderland's new head coach on a two-and-half-year deal.