Aquilani began his career with Italian sideRoma and, after a brief loan spell atTriestina, returned to theSerie A club where he became a regular in the Roma side during the2005–06 season, earning the nickname "Il Principino" (The Little Prince), due to his resemblance to former Roma legendGiuseppe Giannini, both in terms of appearance and playing style, who was known as "Il Principe" (The Prince).[3][4] During the following season, he suffered a thigh injury and was ruled out for several months. In 2007 and 2008 he won consecutiveCoppa Italia titles with Roma, as well as the2007 Supercoppa Italiana.
He moved to English clubLiverpool for the start of the2009–10 season but in August 2010, having received only limited playing time atAnfield due to injury, he returned to Italy and joinedJuventus on loan until the end of the2010–11 season. Aquilani returned to Liverpool at the end of the season as Juventus did not take up their purchase option. He went on loan again in 2011, playing for Italian clubMilan for the2011–12 season, and was subsequently sold toFiorentina in 2012, where he remained until his transfer to Portuguese clubSporting CP in 2015; he returned to Italy in 2016, joining Pescara, and was later loaned toSassuolo for the second half the season. In 2017, he joined Spanish clubLas Palmas, but was released by the club at the end of the season. After a year without a club, he announced his retirement in 2019.
Internationally, Aquilani has represented Italy at various youth levels, while at senior level, he made his full international début in November 2006 in a 1–1 draw againstTurkey. In total, he made 38 appearances for Italy between 2006 and 2014, scoring 5 goals, and also took part atEuro 2008, the2013 FIFA Confederations Cup (winning a bronze medal in the tournament), and the2014 FIFA World Cup with the Italian senior team.
In 2001, when Aquilani was 17,Chelsea andArsenal offered him contracts, but he declined the offers to continue playing for his youth clubRoma.[5]
He made his debut inSerie A at the age of 18 on 10 May 2002 under then managerFabio Capello againstTorino. Roma won that game 3–1. He was loaned toSerie B clubTriestina for the 2003–04 season to gain first team experience.
Returning to Roma in the 2004–05 season, Aquilani broke into the starting XI. On 31 March 2005, he signed a new five-year contract with Roma, which worth €1.1 million, €1.25M, €1.48M, €1.61M and €1.79M respectively from 2005 to 2010 in gross annually.[6] In the 2005–06 season, he scored the second goal in thederby victory on 26 February 2006, a victory in which Roma broke the record for the most consecutive wins in Serie A,[7] a record later broken byInter Milan in the 2006–07 season.
In thefollowing season, Aquilani was expected to be one of Roma's best players. He was given the number 8 shirt previously worn byMatteo Ferrari. Unfortunately, aninjury forced him out of the game for several months.[8][9] Aquilani returned to the field in May 2007 and featured in three games towards the end of the season, including the last two.
He scored two long range goals in the first two matches of the2007–08 season againstPalermo andSiena.[10] Although he was injured in October 2007,[11] he returned to the squad in January 2008.
Aquilani was injured again on 22 October 2008 againstChelsea.[12] He returned to action on 11 January 2009 againstMilan but picked up another injury in February.[13] Although he played against Arsenal as a last minute substitute on 11 March 2009,[14] he did not play any part for the rest of the season.
On 26 May 2009, Aquilani signed a new contract with Roma until 2013, adding three more years to previous deal. He was offered an annual gross salary of €3.2 million for 2008–09 season; €3.6 million in 2009–10 season; €3.9 million in 2010–11 season and ultimately €4.2 million in the last two-year of the contract.[15][16]
On 5 August 2009,Liverpool announced that they had agreed a deal with Roma for the transfer of Aquilani, subject to amedical test.[17][18] The club subsequently announced that the player had passed the medical test and signed a five-year contract on 7 August 2009.[19] Roma revealed that the fee was €20 million (£17 million) plus sporting bonus.[20] Aquilani was handed the number 4 shirt, last worn bySami Hyypiä, who joinedBayer Leverkusen at the end of the 2008–09 season.
Martin Škrtel and Aquilani warming up before the game between Liverpool and Roma.
Aquilani made his Liverpool reserves debut with a 15-minute substitute appearance in a 2–0 win againstSunderland reserves on 21 October 2009.[21] His first game for Liverpool was a 2–1 4th round League Cup defeat toArsenal, coming on in the 77th minute forDamien Plessis.[22] He made hisPremier League debut on 9 November, as a late substitute againstBirmingham City in a 2–2 draw.[23] Aquilani made his first start againstFiorentina in aChampions League match on 9 December 2009, where Liverpool lost 2–1.[24] Aquilani made his first Premier League start againstWolves on 26 December 2009 and received a standing ovation fromthe Kop when he was substituted in the 84th minute forDaniel Pacheco.[25]
Aquilani next started for Liverpool in their 2–0 win overBolton Wanderers, where he got his second assist for Liverpool, again setting upDirk Kuyt. He scored his first goal for Liverpool on 15 March 2010 againstPortsmouth and he also assistedFernando Torres for the fourth Liverpool goal. He was votedman of the match by the fans on Liverpool's official website. Aquilani also gained the man of the match award in his next Liverpool league start, againstFulham in a goalless draw atAnfield. In his next start for Liverpool he finished the match with three assists during a 4–0 away win againstBurnley On 29 April 2010 he scored a goal againstAtlético Madrid in theEuropa League, cancelling out Atlético's first leg goal fromDiego Forlán by scoring moments before half-time. Despite a great performance from Aquilani on the night, Liverpool eventually went out of the semi-finals on the away goal rule afterYossi Benayoun had put Liverpool 2–0 up, as Forlán scored his second of the tie in extra-time to take the aggregate score to 2–2.[26] Aquilani won the LFC Man of the Match award again after his performance.[27]
Aquilani also played in Liverpool's last 2 games of the season, a 2–0 defeat at the hands ofChelsea at Anfield[28] and a goalless draw away toHull City at theKC Stadium.[29] In total, Aquilani played 26 times in his debut season for the reds, scoring twice but rarely playing the full 90 minutes.
With the departure ofRafael Benítez in June 2010, new managerRoy Hodgson played him in the pre-season, but stated publicly in mid-August that Aquilani may go back to his native Italy on loan for a full season, where he could gain match fitness through regular appearances.[30]
On 21 August 2010, a deal between Liverpool andJuventus was agreed, to allow Aquilani to go on a one-season loan deal to Juventus with an option of a permanent move.[31][32][33][34] He made his debut for theBianconeri on 12 September in a 3–3 draw withSampdoria from coming on as a substitute forSimone Pepe. He came on as a sub again on 23 September in a 3–1 home defeat to Sicilian clubPalermo. His first start for the club came on 26 September in a 4–2 win againstCagliari. After that Aquilani played 80 minutes against reigning championsInter Milan in a goalless draw before he scored his first goal for the club on 17 October in a 4–0 home win againstLecce two weeks later. He played his first full 90 minutes away toBologna in another 0–0 draw. On 5 February, he played the full 90 minutes in a 3–1 away win over Cagliari with his next match being against Inter in a 1–0 win. On 21 April,Kenny Dalglish claimed Aquilani still had a future at Liverpool,[35][36] despite claims that he wanted to remain in Italy. Aquilani returned to Liverpool after Juventus decided against making his transfer permanent.[37]
On 4 July 2011, Aquilani started pre-season training with Liverpool, though his agent later confirmed that his wish was to stay at Juventus in Serie A. He was included in the squad's pre-season tour of Asia and marked his return to the team in a friendly againstGuangdong Sunray Cave on 13 July.[38][39] He subsequently impressed against a Malaysian XI on 16 July 2011.[40]
On 25 August 2011, Aquilani joinedAC Milan on loan for the 2011–12 season with Milan having an option to make the move permanent at the end of the season, despite pulling a string of impressive performances during the pre-season tour in Asia.[41][42] Liverpool managerKenny Dalglish paid tribute to Aquilani on his departure, stating that the only reason for the loan was an inability to fit the player into the team's preferred formation.[43] Damien Comolli, Liverpool director of football, said, "I want to pay tribute to the way Alberto has conducted himself during these discussions. Throughout the entire process, his only desire has been to play football and he has put this ahead of any other considerations and at personal cost to himself."[42]
Aquilani made his debut for theRossoneri in the opening game of the 2011–12 season againstLazio, and had an immediate impact by being involved in the build-up for Milan's first goal with a neat pass toAntonio Cassano, and assisting the second goal himself from a corner-kick. On 13 September 2011, he made his European debut for Milan in theUEFA Champions League againstFC Barcelona at theCamp Nou, coming off the bench to help Milan secure a 2–2 draw. On 18 September 2011, Aquilani scored his first goal for Milan in his second Serie A match for the club, heading home a cross from Cassano to open the scoring againstNapoli at theSan Paolo inNaples.[44]
Aquilani returned to Liverpool for pre-season training in preparation for their2012–13 season. He was included in the squad for Liverpool's pre-season tour of North America and played 45 minutes in the opening match againstToronto FC.[45] The club accepted an undisclosed fee for the midfielder fromFiorentina in Italy, and his transfer was completed on 3 August 2012.[46] Following the transfer, Aquilani averred that only an excessive price that Liverpool had placed on him had prevented him completing permanent moves toAC Milan andJuventus following his successful loan spells.[47] Fiorentina revealed that Aquilani had only cost the club €790,000 as other cost. Liverpool allowed Aquilani to leave the club for free thus Roma also received nothing from the bonus clause.[48]
On 26 January 2014, in a match againstGenoa, Aquilani scored his first career hat-trick in a thrilling 3–3 draw.[49] Aquilani reached the2014 Coppa Italia Final with Fiorentina thatseason, where they were defeated by Napoli. Thefollowing season, Fiorentina finished the league in fourth place for a third consecutive season, while also reaching the semi-finals of the2014–15 UEFA Europa League.
Following the conclusion of the 2014–15 season with Fiorentina, Aquilani became a free agent after his contract was not renewed. In August 2015, he signed with Portuguese clubSporting CP on a three-year contract, reportedly worth €1 million per season.[50]
On 25 August 2017 and following his departure from Pescara, Aquilani signed a two-year contract with SpanishLa Liga sideLas Palmas.[54] In July 2018,following the club's relegation, Aquilani was released from his contract.[55]
On 28 June 2019, after one season without a club, Aquilani announced his retirement.[56]
In Italy'sUEFA Euro 2012 qualification campaign, Aquilani played his first game in a 1–0 away win againstSlovenia on 25 March 2011, playing for the full 90 minutes.[65] He also started in Italy's next match at home againstEstonia on 3 June, but came off in the first half of the 3–0 win due to ahead injury.[66] On 10 August 2011, he scored his third international goal with the late winner in afriendly against defending world champions Spain.[67]
Aquilani took part at the2013 FIFA Confederations Cup under managerCesare Prandelli, where Italy managed a third-place finish; in the victorious bronze medal match againstUruguay, he converted a penalty in the resulting shoot-out.[68]
On 11 October 2013, Aquilani scored the late equalizing goal in Italy's 2–2 away draw againstDenmark during the team's2014 FIFA World Cup qualifying campaign; this was his fifth goal for Italy.[69] He was an unused member of Italy's2014 FIFA World Cup squad,[70][71] as the Italians suffered a group-stage elimination.[72]
Aquilani was a modern, hard-working and versatileplaymaker who was capable of functioning in a number ofmidfield roles, from aholding role as adeep-lying playmaker, to a more advancedtrequartista orattacking midfielder.[73][74][75] His favoured position was that of an offensive-mindedcentral midfielder orbox-to-box midfielder, a position known as the "mezz'ala" role, in Italy, which enabled him to make late attacking runs from behind into the penalty area or create space for team-mates with his movement, despite his lack of notable pace or physicality; he was also used on thewing, or even as awing-back on occasion.[76][77][78] With the Italy national team, he was also deployed in a different role, as afalse-attacking midfielder on occasion, under manager Cesare Prandelli.[79] Throughout his career, Aquilani drew praise for his vision, creativity, technique, quick incisivepassing, which enabled him to dictate the tempo of his team's plays in midfield, and was also noted for his energy and long-rangeshooting ability with either foot.[73][77][80][81][82] Due to his eye for goal, height, and heading accuracy, he was also effective in the air, and was also accurate from set-pieces, which enabled him to contribute to his team's offensive play with additional goals from midfield.[77][82] Despite his talent in his youth, he was often injury prone throughout his career, which limited his playing time and affected his fitness and consistency, and as a result, he has been accused by some in the sport of not living up to his initial potential.[83]
On 11 July 2019, Aquilani was announced as the head coach ofFiorentina's under-18 team,[84] remaining in that position until December, when he joined the first team staff as an assistant toGiuseppe Iachini. On 19 July 2020, he was appointed as head coach of thePrimavera squad.[85] On 26 August 2020, the side successfully defended theCoppa Italia Primavera title, beating Hellas Verona 1–0 in the final.[86]
In 2023, he left Fiorentina's youth system to embark on a career as a first team head coach, taking over atSerie B clubSC Pisa.[87] After guiding Pisa to a mid-table place in the league table, Aquilani parted ways with the club in June 2024.[88]
After a season without a job, in June 2025, Aquilani was appointed in charge of Serie B clubCatanzaro, replacingFabio Caserta.[89]
Aquilani marriedMichela Quattrociocche on 4 July 2012.[90][91] Together, they have two daughters: Aurora (b. 2011)[92] and Diamante (b. 2014).[93] On 11 May 2020, it was announced that the two had separated.[94]