Alberto Aquilani, a former Liverpool midfielder, has won his fifth trophy in just three years as head coach of Fiorentina's Under 19s team, surpassing his previous record of five. When Aquilani took over in July 2020, it only took him a month to win his first trophy, the Coppa Italia Primavera. With a 2-1 victory over Inter Milan on Wednesday, Aquilani earned his second Primavera Super Cup title. This indicates that he has already surpassed the total number of awards he won as a player.

The Italian made a name for himself at Roma before spending £20 million to move to Liverpool in 2009. However, he left the Reds three years later as one of their greatest flops of modern times. The midfielder made just 28 appearances in two seasons with the Reds' first team.

After being rejected by Roy Hodgson, he went on loan to AC Milan and Juventus before signing a permanent deal with Fiorentina. There he was a great asset to the club improving the performance of the team as a whole. In his first season at Anfield, Aquilani occasionally impressed, scoring in the Reds' Europa League semi-final win over Atletico Madrid. However, after Aquilani's first season on Merseyside, his predecessor, Rafa Benitez, left the club, and Hodgson made it abundantly clear that the Italian had fallen down the hierarchy.
According to reports, Hodgson told Aquilani that he preferred Joe Cole to play in his position, and he only selected Cole for two games in the early stages of the 2010–11 season before sending him on loan to Juventus. Now, Aquilani has stated that he is dissatisfied with the fact that Liverpool fans will always remember him as a failure even though he was influential in his time.