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He played his youth soccer career for the Renato Curi Angolana football club in the mid-1990s.
Grosso was born in Rome but hails from Chieti, Abruzzo, where his family soon returned to. Grosso joined Renato Curi Angolana in 1994 and played in the club's youth system until 1995. He was promoted to the senior squad for the 1995–96 season and soon became a key part of the first team. Following the 1997–98 season, he left the Eccellenza club to join Chieti for an undisclosed transfer fee. Grosso made 108 official appearances for Renato Curi, scoring a very impressive 47 goals as an attacking midfielder and left winger.
In summer 1998, Grosso transferred to Chieti of Serie C2. An attacking midfielder at the time, he again impressed in his three-season spell with Chieti. He scored 17 goals in 68 league appearances. Following several impressive performances, he was scouted by Serie A club Perugia in 2001, and in mid-summer, Grosso officially transferred to the club.
In July 2001, Grosso officially joined Perugia. In his debut Serie A season, he made 24 appearances and scored one goal. By now, he had been converted into a left wing-back by head coach Serse Cosmi and in his second season in Perugia, he maintained a starting position and made 30 league appearances, scoring four goals. In his third season with Perugia, Grosso made just 12 appearances in the first six months of the 2003–04 season. To some surprise, Grosso transferred from Perugia in January 2004 to Palermo, which at the time played in Serie B. In 2003, during his time with Perugia, Grosso earned his first Italy cap.
Grosso made his international debut with the Italy national team on 30 April 2003 in a 2–1 friendly away win over Switzerland, under head coach Giovanni Trapattoni. He scored his first goal for Italy in a 1–1 away draw against Scotland, on 2 September 2005, in a 2006 FIFA World Cup qualifying match.
During the winter transfer window in January 2004, Grosso transferred to the Sicilian side and they earned promotion at the conclusion to the season. Grosso made 21 appearances for his new club in the latter portion of the 2003–04 season, scoring one goal, as the club won the Serie B title.
From 2005 onwards, Grosso became a regular member of the starting line-up at left-back under Marcello Lippi, and was called up to represent Italy at the 2006 FIFA World Cup by Lippi, playing a key role throughout the tournament as the Italians went on to win the title.
In July 2006, Grosso joined Inter for a reported €5 million transfer fee (plus Paolo Dellafiore). However, Grosso was in-and-out of the club's starting line-up and was mostly used as a substitute. He made just 23 appearances for Inter in the league, and scored two goals, as the team captured the 2006 Supercoppa Italiana and the Serie A title. Following the disappointing season with Inter, Grosso opted to move abroad and was sold to Olympique Lyonnais in the summer of 2007, just one year after his move to Inter.
On 4 July 2006, Grosso scored the first goal against hosts Germany in the 119th minute of the World Cup semi-finals with a curling left-footed strike beyond the reach of Jens Lehmann into the Germans' net from the edge of the box, which commentator John Motson would describe as "magnificent", while Grosso ran about screaming "Non ci credo!" ("I don't believe it!") as his teammates celebrated. In the World Cup final, five days later, he scored the winning penalty against France in a 5–3 victory in the resulting shoot-out after a 1–1 draw following extra-time, which allowed the Italy national team to win their fourth World Cup title.
In July 2007, Grosso moved abroad and signed a four-year contract with Lyon of the French Ligue 1 after passing a medical and agreeing personal terms. The transfer fee was €7.5 million He was issued the number 11 shirt. His first season with proved a successful one as he was a key part of the club's starting line-up in both the UEFA Champions League and Ligue 1, and saw him win the league title, the Coupe de France, and the Trophée des Champions. In his second season with Lyon, Grosso was limited to just 22 league appearances, partially due to injury, but was heavily linked with a move back to Italy during the 2009 summer transfer window. In August 2009, he officially returned to Italy, joining Juventus.
On 31 August 2009, it was confirmed Grosso had returned to Serie A to join Juventus following his two-year spell in France. After chasing the defender all summer long, the parties struck a deal on the final day of the transfer market at a €2 million fee plus bonus up to €1 million. He was instantly inserted into Juventus' starting XI and began the season in good form. He scored his first goal in a league game against Udinese in November 2009. He made 28 appearances during the season and scored two goals.
In injury time of the round of 16 fixture against Australia, with the score tied at 0–0, Grosso advanced with the ball into the box from the left flank and was fouled in the penalty area by Lucas Neill, who went to ground, causing Grosso to stumble. Francesco Totti subsequently converted the decisive penalty issued by referee Luis Medina Cantalejo, as a ten-man Italy won the match 1–0 to advance to the quarter-finals. However, Grosso was accused of diving by some media outlets. In 2010, Grosso sat down with an Australian media outlet where he said he did not stay on his feet because he was exhausted and "didn’t have the strength to go forward", he said he "felt contact, so I went down" and "maybe I accentuated it a little bit", but insisted that after reviewing the replay that Neill did commit a foul.
At the start of the 2013–14 season, it was announced Grosso would take up a coaching position in the Juventus youth system. On 11 March 2014, he was appointed as the new manager of the Juventus Primavera (U-19) youth team following a string of poor performances under manager Andrea Zanchetta, who was transferred to another position within the youth system.
On 13 June 2017, Grosso was named head coach of Bari in Serie B. The following April, his home was vandalised by fans of local rivals Pescara, who hanged a rooster, the mascot of his club. The team finished 7th and were eliminated from the playoffs by Cittadella.
On 21 June 2018, Grosso was appointed manager of Hellas Verona, signing a two-year deal at the newly relegated Serie B club. He was sacked the following 1 May after a shock 3–2 home loss to relegation-threatened Livorno.
On 5 November 2019, Grosso was appointed manager of Serie A club Brescia. He was sacked on 2 December after three straight defeats without a single goal.
On 25 August 2020, Grosso was appointed the manager of Swiss side Sion.
Celebrating Fabio Grosso's birthday. Wishing him all the best!