- Midfielder for U.S. Lecce (1985-1991) and Juventus F.C. (1991-2004); in all 512 games and 46 goals.
- Won five Serie A (1995, 1997, 1998, 2002, 2003), four Supercoppa Italiana (1995, 1997, 2002, 2003), the UEFA Champions League (1996), the Intercontinental Cup (1996), the UEFA Cup (1993), the UEFA Intertoto Cup (1999) and the Coppa Italia (1995) with Juventus F.C..
- 20 appearances for Italy National Football Team (1994-1996, 1999-2000); scored 2 goals. Member of the Euro 2000, and the USA '94 squads.
- Member of Italy national team who finished runner-up at the 1994 FIFA World Cup and the 2000 UEFA Euro.
- Captain of Juventus F.C. from 1996-2004.
- 2004: Retired from football at the age 35.
- Played well over 400 games for Juventus F.C..
- Played well over 350 games at Serie A.
- Descended to Serie B with U.S. Lecce in 1986 and 1991.
- Promotion with U.S. Lecce to Serie A in 1988.
- Worked as assistant for Siena from 2005-06.
- Head coach of Arezzo (2006, 2007), Bari (2007-2009), Atalanta (2009-10), Siena (2010-11), Juventus F.C. (2011-2014), Italy National Football Team (2014-2016), Chelsea F.C. (England, 2016-2018), Inter Milan (2019-2021) and Tottenham Hotspur F.C. (England, 2021-).
- Has a daughter called Vittoria (b. 2007) with his wife Elisabetta Muscarello.
- As a coach, he won the Serie B (2009) with Bari; 3 Serie A (2012-2014), 2 Supercoppa Italiana (2012, 2013) and the runner-up of the 2012 Coppa Italia with Juventus F.C.; Premier League (2017) and FA Cup (2018) with Chelsea F.C.; Serie A (2021) and the runner-up of the UEFA Europa League (2020) with Inter Milan.
- Won the Panchina d'Argento in 2009.
- Named the Serie A Coach of the Year four times (2012-2014, 2021).
- Won the 2013 Globe Soccer Award as the Best Coach of the Year.
- Won the 2015 Gazzetta Sports Award as the Coach of the Year.
- Won the 2017 London Football Award as the Manager of the Year.
- Won the 2016/17 Premier League Manager of the Season award.
- Won the 2016/17 LMA Manager of the Year award.
- Won the Special Achievement at the 2017 GQ Men of the Year Award.
- Finished 2nd Place at the 2017 The Best FIFA Men's Coach.
- Inducted into the Italian Football Hall of Fame in 2021.
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