|Date of birth||6 September 1979|
|Place of birth||Galliate, Italy|
|Height||1.80 m (5 ft 11 in)|
|1998||→ Modena (loan)||0||(0)|
|1998–1999||→ Prato (loan)||21||(4)|
|1999||→ Varese (loan)||3||(0)|
|1999–2000||→ Prato (loan)||28||(20)|
|2004||→ Parma (loan)||7||(0)|
|2005||→ Siena (loan)||11||(6)|
|* Senior club appearances and goals counted for the domestic league only and correct as of end of 1314 season.
† Appearances (Goals).
Maccarone started his career at AC Milan's youth system. In 1998, he went on loan to Modena, but did not make a single appearance. In 1999, he was transferred to Serie C2 team Prato (in a co-ownership deal), scoring 20 goals in 28 league matches. In 2000, he was bought back by Milan and transferred to Empoli F.C., 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 Italian 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.
In 2002 he played twice for Italy. In one of these appearances he came on as a late substitute against England 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 was an unused substitute when Middlesbrough won the 2004 Football League Cup Final. Despite showing fine early form in his first few matches for Middlesbrough, the remainder of his spell at the club was a struggle to justify his price tag and during the first half of the 2004–05 season he was loaned out to Serie A club Parma, and in January 2005 to Siena.
Maccarone returned to Middlesbrough for the 2005–06 season, and despite not being a regular first-team player, endeared himself to the Middlesbrough fans, especially through his work-rate and attitude. The player's spell at Middlesbrough is remembered for two last minute winners in key UEFA Cup ties in 2006. He scored against Basel in the second leg of the quarter-finals, a tie in which Middlesbrough overturned a three-goal deficit to win 4–3 on aggregate. In the semi-final of the same competition he came on as a substitute and scored twice in the aggregate 4–3 win over Steaua Bucharest, once again in the 90th minute, taking Boro to the final in Eindhoven, in which he came on as a substitute. Following his exploits in the semi-final, fellow Middlesbrough striker Jimmy Floyd Hasselbaink declared "Massimo, I love him until I die... it's unbelievable".
Despite these heroics, he made few appearances for Middlesbrough in the following season and in January 2007, Maccarone moved to Siena in a free transfer, signing a three-year contract. In February 2007, he made headlines by criticising former Middlesbrough and then-England manager Steve McClaren for his "ineptitude", causing his club's chairman Steve Gibson to call Maccarone "a fool".
On 11 February 2007, he played his first Serie A match after his Siena return, against Cagliari. Maccarone scored a brace in the 4–3 defeat against A.C. Milan on 17 February, to register his first goals for Siena. He finished the season with six goals, and added 13 in the following (club best by a long margin), as Siena achieved two consecutive 13th league places. After the club was relegated at the end of the 2009–10 season, Maccarone agreed a move to Sicilian Serie A club Palermo, signing a three-year deal with the rosanero, for €4.5 million.
His stint at Palermo however turned out to be a disappointing one, with only two league goals in 18 games, leading the Sicilians to put him into transfer.
From January 2012 to June 2014 Maccarone returned to Empoli in temporary deal. His contract was also extended to 30 June 2015 in 2012 financial year. On 17 July 2014 he was allowed to join Empoli on free transfer.
- "Big Mac al Parma L'ha deciso lui" (in Italian). La Gazzetta dello Sport. 1 September 2004. Retrieved 2009-07-10.
- "Maccarone signs in". BBC Sport (British Broadcasting Corporation). 9 July 2002. Retrieved 7 February 2012.
- "Montella stuns England". BBC. 27 March 2002. Retrieved 21 January 2013.
- "Boro lift Carling Cup". BBC News. 29 February 2004.
- "Maccarone makes switch to Siena". BBC Sport (British Broadcasting Corporation). 4 January 2005. Retrieved 7 February 2012.
- "Middlesbrough 4–1 Basle (agg 4–3)". BBC. 6 April 2006. Retrieved 23 October 2009.
- "M'brough 4–2 S B'chrst (agg 4–3)". BBC. 27 April 2006. Retrieved 23 October 2009.
- Middlesbrough, Sevilla advance to UEFA Cup final
- "Maccarone è bianconero". AC Siena (in Italian). 30 January 2007. Retrieved 4 September 2010.
- Gibson: "Massimo's a fool"
- "Tactical Formation". Football-Lineups.com. Retrieved 15 February 2007.
- "Siena 3–4 AC Milan". ESPNSoccernet. 17 February 2007. Retrieved 8 February 2012.
- US Città di Palermo Report and Accounts on 30 June 2010 (Italian)
- "MASSIMO MACCARONE NUOVO ACQUISTO DEL PALERMO" (in Italian). US Città di Palermo. 15 June 2010. Retrieved 2010-06-15.
- "MACCARONE CEDUTO ALLA SAMPDORIA" (in Italian). US Città di Palermo. 24 January 2011. Retrieved 24 January 2011.
- "Massimo Maccarone alla Sampdoria a titolo definitivo" (in Italian). UC Sampdoria. 24 January 2011. Retrieved 6 July 2014.
- Relazione sulla Gestione of UC Sampdoria Report and Accounts on 31 December 2010 (Italian)
- "Massimo Maccarone ceduto all'Empoli a titolo temporaneo" (in Italian). UC Sampdoria. 26 January 2012. Retrieved 6 July 2014.
- "Maccarone torna all'Empoli, Scappini va al Pisa" (in Italian). UC Sampdoria. 31 August 2012. Retrieved 6 July 2014.
- "Regini torna alla Samp, Maccarone in prestito ad Empoli" (in Italian). UC Sampdoria. 20 June 2013. Retrieved 6 July 2014.
- UC Sampdoria SpA bilancio (financial report and accounts) on 31 December 2012 (Italian)
- "Rescissione consensuale del contratto di Massimo Maccarone" (in Italian). UC Sampdoria. 17 July 2014. Retrieved 17 July 2014.
- "Massimo Maccarone ha firmato" (in Italian). Empoli FC. 17 July 2014. Retrieved 17 July 2014.