Aquilani began his career at Roma and, after a brief loan spell at Triestina, returned to the Serie A club where he became a regular in the Roma side during the 2005–06 season. During the following season, he suffered a thigh injury and was ruled out for several months. He moved to Liverpool for the start of the 2009–10 season, in a deal that including add ons, could potentially be worth £20m in total. In August 2010, having received only limited playing time at Anfield, he joined Juventus on loan until the end of the season. Aquilani returned to Liverpool at the end of the season as Juventus did not take up their purchase option. Having played for Liverpool during their pre-season tours, it was then announced that Aquilani would be returning to Serie A on loan again, this time with AC Milan.
Internationally, Aquilani has represented Italy at youth level and at the Euro 2008. He made his full international debut in November 2006 in a 1–1 draw against Turkey.
In 2001, at the age of 16, Chelsea and Arsenal offered him contracts, but he declined the offers to continue playing for his youth club Roma.
He made his debut in Serie A at the age of eighteen on 10 May 2002 under then manager Fabio Capello against Torino. Roma won that game 3-1. He was loaned to Serie B club Triestina for the 2003–04 season to gain first team experience.
Returning to Roma in the 2004–05 season, he broke into the starting XI. In the 2005–06 season, he scored the second goal in the derby victory on 26 February 2006, a victory in which Roma broke the record for the most consecutive wins in Serie A, a record later broken by Internazionale in the 2006–07 season.
In the following season, Aquilani was expected to be one of Roma's best players. He was given the number 8 shirt previously worn by Matteo Ferrari. Unfortunately, an injury forced him out of the game for several months. Aquilani returned to the field in May 2007 and featured in three games towards the end of the season, including the last two.
He also played in the Champions League against Real Madrid, where he had an excellent game.[citation needed] He scored two long range goals in the first two matches of the 2007–08 season against Palermo and Siena.[citation needed] Although he was injured in October 2007, he returned to squad in January 2008.
Aquilani was injured again on 22 October 2008 against Chelsea. He returned to action on 11 January 2009 against Milan but picked up another injury in February. Although he played against Arsenal as a last minute substitute on 11 March 2009,the did not play in 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.
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