1970: Born May 29 in Schaffhausen, Switzerland, to Italian parents.
1988: Starts career as a midfielder with Schaffhausen.
1991: Joins FC Zurich.
1992: Joins FC Aarau and wins the Swiss Super League in his only season at the club.
1993: Moves to Lazio in Serie A.
1994: November - Makes Italy debut as a substitute in a 2-1 defeat to Croatia in qualifying for Euro 96.
1996: Joins Chelsea, then managed by Ruud Gullit.
1997: April - Scores his first international goal in a World Cup qualifier against Poland which Italy won 3-0.
May 17 - Scores what was then the fastest ever goal in an FA Cup final, netting after 42 seconds against Middlesbrough as Chelsea go on to win 2-0.
1998: March 29 - Scores as Chelsea again beat Boro 2-0 to win the League Cup.
May 13 - Wins Cup Winners' Cup with 1-0 win over Stuttgart in the final.
2000: May 20 - Scores the only goal of the game against Aston Villa to win the FA Cup for a second time.
2002: February - Retires due to injury aged 31 after failing to recover from a broken leg he suffered 18 months earlier in a UEFA Cup tie with St Gallen.
2008: July - Appointed manager of MK Dons in League One.
2009: May - Misses out on promotion as the Dons lose their play-off semi-final on penalties to Scunthorpe.
June - Appointed manager of Championship side West Brom.
2010: May - Wins promotion to the Premier League as the Baggies finish second in the Championship.
2011: February - Sacked by West Brom.
June - Appointed assistant manager to Andre Villas-Boas at Chelsea.
2012: March - Named the Blues' interim coach after Villas-Boas was sacked.
May 5 - Wins the FA Cup as Chelsea beat Liverpool 2-1 in the final.
May 19 - Leads Chelsea to the greatest achievement in the club's history as they win the Champions League by beating Bayern Munich on penalties in Munich.
June 13 - Appointed Chelsea's permanent manager and first-team coach on a two-year contract.
Nov 21 - Chelsea announce they have parted company with Di Matteo, the night after a 3-0 Champions League defeat to Juventus makes their qualification out of the group stages unlikely.