After playing for several smaller Italian clubs, such asRenato Curi,Chieti andPerugia, he made his breakthrough during his two seasons as aleft-back withPalermo, which earned him a move to defendingSerie A championsInter Milan in 2006. During his only season with Inter, he helped the club defend the Serie A title and win theSupercoppa Italiana. He later also won titles withLyon in France and withJuventus. Grosso retired in 2012 after winning theScudetto with Juventus.
At international level, Grosso made 48 appearances forItaly and scored the decisive late first goal againstGermany in the2006 World Cup semi-final. In the 95th minute of the match vs Australia, he cut inside past Lucas Neill, who slid to block and mistimed his tackle, bringing Grosso down. Totti then scored the resultant winning penalty.
He also scored the winning penalty in thepenalty shootout againstFrance in the final of the tournament which enabled theAzzurri to win the trophy for the fourth time in their history. He also represented Italy atUEFA Euro 2008 and at the2009 FIFA Confederations Cup.
Grosso was born inRome but hails fromChieti,Abruzzo, where his family soon returned to. Grosso joinedRenato 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 theEccellenza club to joinChieti for an undisclosed transfer fee. Grosso made 108 official appearances forRenato Curi, scoring 47 goals as anattacking midfielder andleft winger.
In summer 1998, Grosso transferred to Chieti ofSerie C2. Anattacking midfielder at the time, he again impressed in his three-season spell with Chieti. He scored 17 goals in 68 league appearances. He was scouted bySerie A clubPerugia in 2001, and in mid-summer, Grosso officially transferred to the club.
In July 2001, Grosso officially joined Perugia. In his debutSerie A season, he made 24 appearances and scored one goal. By now, he had been converted into a left wing-back by head coachSerse 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. Grosso transferred from Perugia in January 2004 toPalermo, which at the time played inSerie B.
During the winter transfer window in January 2004, Grosso transferred to theSicilian side and they earned promotion at the conclusion to the season. Grosso made 21 appearances for his new club in the latter portion of the2003–04 season, scoring one goal, as the club won the Serie B title.
Palermo'sfirst season in Serie A was very successful as the club managed a very impressive sixth-place finish, losing just nine matches and also qualifying for theUEFA Cup. Grosso contributed as a regular starter, making 36 league appearances, also scoring a single goal. During the2005–06 Serie A season, Grosso made 33 appearances for his club as Palermo impressed, finishing eighth in Serie A. He was one of four Palermo players who madeMarcello Lippi's2006 FIFA World Cup-winning squad, but at the conclusion of the tournament, Grosso was sold toInter Milan.[4]
In July 2006, Grosso joined Inter for a reported €5 million transfer fee (plusPaolo Dellafiore).[5] 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 the2006 Supercoppa Italiana and theSerie A title. Following the disappointing season with Inter, Grosso opted to move abroad and was sold toLyon in the summer of 2007, just one year after his move to Inter.
In July 2007, Grosso moved abroad and signed a four-year contract with Lyon of the FrenchLigue 1, after passing a medical and agreeing personal terms. The transfer fee was €7.5 million.[6] He was issued the number 11 shirt.[7] In his first season, he was part of the club's starting line-up in both theUEFA Champions League and Ligue 1, and won theleague title, theCoupe de France andthe 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.[8] In August 2009, he officially returned to Italy, joiningJuventus.
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.[9] He was instantly inserted into Juventus' starting XI, and began the season in good form. He scored his first goal in a league game againstUdinese in November 2009. He made 28 appearances duringthe season, and scored two goals.[10]
In the2010–11 season, Juventus released several elder players, but Grosso reportedly refused any transfer. Juve youth productPaolo De Ceglie took back the starting place and Grosso was frozen out from the start of season, as well as being excluded from 25-man squad for2010–11 UEFA Europa League.[11] However, after Juventus lost numbers of players due to injury, Grosso andHasan Salihamidžić were recalled for the first time, on 6 November.[12] He made two appearances in his final season, the2011–12 season, as new head coachAntonio Conte either preferred De Ceglie or had a winger or wide midfielder deputize as a fullback or wingback in a 3–5–2 formation. Juventus won the title undefeated that season. Grosso's contract ended in the summer of 2012 and he opted to retire from professional football.[10]
From 2005 onwards, Grosso became a regular member of the starting line-up at left-back underMarcello Lippi, and was called up to represent Italy at the2006 FIFA World Cup by Lippi, playing a key role throughout the tournament as the Italians went on to win the title.
In injury time of the round of 16 fixture againstAustralia, 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 byLucas Neill, who went to ground, allowing Grosso to dive.Francesco Totti subsequently converted the decisive penalty issued by refereeLuis Medina Cantalejo, as a ten-man Italy won the match 1–0 to advance to the quarter-finals.[15] However, Grosso was accused ofdiving by many media outlets.[15][16][17][18] 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".[19]
On 4 July 2006, Grosso scored the first goal against hostsGermany in the 119th minute of the World Cup semi-finals, with a curling left-footed strike beyond the reach ofJens Lehmann into the Germans' net from the edge of the box, which commentatorJohn Motson would describe as "magnificent", while Grosso ran about screaming "Non ci credo!" ("I don't believe it!") as his teammates celebrated.[20][21] In theWorld Cup final, five days later, he scored the winning penalty againstFrance 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 fourthWorld Cup title.[22]
Grosso was also included inRoberto Donadoni's 23-man Italy squad forUEFA Euro 2008.[13] He made a substitute appearance in Italy's opening match of the tournament, a 3–0 defeat to theNetherlands,[23] but was subsequently started in the remaining two group matches, a 1–1 draw againstRomania,[24] and a 2–0 win overFrance,[25] and was praised in the Italian media for his performances along the left flank as Italy advanced from the group in second place.[26] In the quarter-final match against eventual championsSpain, he helped the team keep a clean sheet and converted Italy's first penalty in the resulting shoot-out, which Spain won 4–2.[27]
At the start of the 2013–14 season, it was announced Grosso would take up a coaching position in theJuventus 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.[10][33][34]
On 13 June 2017, Grosso was named as head coach ofBari in Serie B.[35] The following April, his home was vandalised by fans of local rivalsPescara, who hanged a rooster, the mascot of his club.[36] The team finished seventh and were eliminated from the playoffs byCittadella.[37]
Grosso was appointed manager ofHellas Verona on 21 June 2018, signing a two-year deal at the newly relegated Serie B club.[37] He was sacked the following May, after a shock 3–2 home loss to relegation-threatenedLivorno.[38]
On 5 November 2019, Grosso was appointed as the manager of Serie A clubBrescia.[39] He was sacked on 2 December after three straight defeats without a single goal.[40]
Grosso was appointed the manager ofSwiss Super League sideSion on 25 August 2020.[41] He was sacked on 5 March 2021, after a 3–0 home loss toLugano as Sion sat in last place in the league.[42]
On 23 March 2021, Grosso was appointed as the manager ofFrosinone.[43] He won the2022–23 Serie B, after which his contract expired; he eventually chose to depart from Frosinone, who instead appointedEusebio Di Francesco in charge for the following Serie A campaign for the club.[44]
On 16 September 2023, Grosso was unveiled as the new manager of Ligue 1 club Lyon, a club at which he formerly played, replacingLaurent Blanc, who was fired 8 days prior.[45] On 29 October 2023, prior to an away match againstrivalsMarseille at theStade Vélodrome, Grosso suffered a facial injury due to shards of broken glass hitting his face after the Lyon bus waspelted with stones on its way to the stadium. He received medical treatment due to heavy bleeding.[46] The match was subsequently postponed by the officials.[47]
Following a short tenure that saw Lyon failing to improve in its results and lying at the bottom of the league table, Grosso was ultimately dismissed from his coaching position on 30 November 2023.[48]
A formerattacking left back, Grosso was a physical, quick, and energetic player, who was sound both defensively and offensively, due to his work-rate, attacking prowess, technique, and stamina, which enabled him to excel as an offensive–minded left-back. A versatile footballer, regarded as one of the top Italian full-backs of his generation, he was also adept with accuratecrossing ability, which even allowed him to be deployed as awinger or as an attackingwing-back on either flank throughout his career, despite being naturally left-footed.[10][51][52][53][54] Unusually for a defender, he was also afree kick,penalty and corner kick specialist, responsibilities usually held by a striker or midfielder.[54][55][56]
^Paolo Menicucci (17 June 2008)."L'Italia si sveglia e vola ai quarti" [Italy wake up and fly on to the quarter-finals] (in Italian). UEFA. Retrieved4 May 2015.
^"Santon in Sud Africa Pazzini resta fuori" [Santon in South Africa Pazzini remains excluded] (in Italian). La Gazzetta dello Sport. 4 June 2009. Retrieved2 September 2016.