‘Il Gladiatore’ holds cult status with Boro fans thanks to two legendary match-winning goals on our incredible journey to the 2006 UEFA Cup final.
Maccarone began his career in AC Milan’s youth system but he did not make an appearance with The Rossoneri. Instead, after a series of loan moves, the striker cut his teeth in the Italian lower leagues, enjoying prolific spells with first Prato and then Empoli.
It was his form helping the latter to promotion from the second tier that saw him become the first Italian player in more than 70 years to make his full international debut before playing in Serie A.
His international debut was against England, winning a late penalty in a friendly match in March 2002. Vincenzo Montella scored it, and the match was won by The Azzuri.
But it was playing for Italy’s Under-21s that Maccarone was earning even more admiring glances from suitors across Europe.
Having scored once against England’s Under-21s in a friendly match, also in March 2002 and shortly before his senior debut with the senior national team, he added another two in a 2-1 victory over the Three Lions in the European Under-21 Championships the following summer. The latter was a stunner, Maccarone beating future Boro man Chris Riggott with a sublime touch and slamming into the far corner.
Among those watching on was Steve McClaren, and the Boro boss saw enough to shell out a club -record £8.15m to secure his signature.
Maccarone made an immediate impact, scoring twice against Fulham in only his second game for the club.
In his first season in English football he scored nine goals in 34 appearances but a combination of a succession of niggling injuries and struggles to adapt to the physicality of the English game led to him losing his First Team place.
He scored just seven goals in 30 games the following season and was ultimately an unused substitute for the team's Carling Cup success against Bolton Wanderers, the striker visibly distraught not to have played his part.
But he would have his moment in a Boro shirt.
After loan periods at Parma and Siena, Maccarone returned to Boro and although he perhaps did not achieve the consistent highs that had once been hoped, he stepped up when it mattered to score two of the most monumental goals in the club's history.
The first was last-gasp winner against FC Basel in the UEFA Cup quarter-final, and then another dramatic late winner against Steaua Bucharest in the semi-final.
The goals instantly entered Boro folklore as lightning famously struck twice at the Riverside, Boro coming from behind to win each tie 4-3 on aggregate.
His heroics led fellow striker Jimmy Floyd Hasselbaink to proclaim "Massimo, I love him until I die...it's unbelievable."
During his time at Boro, Maccarone made 102 appearances and scored 24 goals.
He was released by Boro in January 2007, returning to Siena. Maccarone would turn out for a string of clubs in his homeland, as well as Brisbane Roar as a marquee player in the Australian A-League.