Massimo Maccarone

Early career

Maccarone grew up playing with friends in Oleggio, in the Province of Novara. He was spotted in the final of the "Fortina e Zanolli" youth tournament at the age of eight (Pulcini category). At nine he joined Soccer Boys Turbigo and, at thirteen, was recruited by AC Milan, spending five seasons in the club's academy. He also appeared at the Torneo di Viareggio in 1998. After featuring in pre-season friendlies under Fabio Capello, he spent the summer of 1998 on loan at Modena, where he failed to make an appearance, before moving to Prato in Serie C2 in September 1998. He scored on his debut on 4 October 1998 in a 2–0 win over Cremapergo and finished the season with 21 league appearances and 4 goals; in the play-offs he converted two penalties against Mantova in the semi-finals, before Prato lost the final. He began the following season with Varese but returned to Prato on 27 September 1999. He scored 20 goals in 28 league matches to finish as Serie C2's top scorer. Prato reached the promotion play-off final but lost 3–2 to Alessandria on 11 June 2000; Maccarone scored Prato's first goal in the match. In 2000, Maccarone returned to Milan and transferred to Empoli, helping the club get promoted to Serie A during the 2001–02 season. In the same period, he was one of the most outstanding players of the Italy U21 team which reached the semi-finals in the 2002 UEFA European Under-21 Football Championship. As a result, he was noticed by several teams.

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During his time at Empoli, Maccarone made his debut with the Italy Under-21 side under Marco Tardelli. He later earned a place as a starting striker in Claudio Gentile's Italy Under-21 side between 2000 and 2002. In total, he scored 11 goals with the Under-21 side in 15 appearances, and he took part at the 2002 Under-21 European Championship with Italy, where he finished as the tournament's top scorer, with 3 goals, helping Italy to reach the semi-finals, where they lost out to the eventual champions, the Czech Republic. During the group stage, he scored two goals in a 2–1 win against the England Under-21 side in Basel. In 2002, he played twice for the Italy senior side. He made his senior international debut on 27 March, in a friendly match against England in Leeds; he came on as a late substitute, with the score level at 1–1. In injury time, Maccarone was fouled in the area by the English goalkeeper David James, allowing Vincenzo Montella to score the winning goal from the penalty spot. Maccarone had scored a goal in a 1–1 friendly draw in Bradford against the England Under-21 side earlier that week. It had been over seventy years that a Serie B player had made his debut with the Italy national side before making his Serie A debut. He made his second and final appearance for the Italian senior side on 16 October 2002, in a 2–1 away defeat against Wales in a European Championship qualifying match.

Maccarone predominantly played as a striker, although he was also capable of being deployed as a supporting forward or as a winger, where he was able to move into the center of the pitch and curl shots towards goal with his stronger foot, due to his striking ability from distance, and his eye for goal. Maccarone was capable of shooting with either foot, and he possessed good tactical intelligence, pace, and technique, as well as a strong mentality and good composure in front of goal; however, he was effective in the air.

Following his retirement, he stayed on at Carrarese as a technical collaborator under his former boss Silvio Baldini for the 2020–21 season, leaving in April 2021 following the appointment of Antonio Di Natale as the club's new head coach. In June 2022, Maccarone took on his first role as head coach, accepting a job offer from Tuscan Serie D amateurs Ghiviborgo. After a single season at Ghiviborgo, Maccarone was named new head coach of Serie D fallen giants Piacenza; he was however dismissed from his coaching post just a few months later, on 12 November 2023, following a negative start to the club's league campaign.