Montella's nickname during his playing career was "Aeroplanino", in reference to his small stature and trademark goal celebration, in which he spread his arms like wings.

He is mostly remembered for his performances with Roma (1999–2007), where he won the Serie A title and the Supercoppa Italiana during the 2000–01 season, also later reaching the 2003 Coppa Italia final with the club.

[9] At international level, he made 20 appearances for Italy between 1999 and 2005, scoring three goals; he was notably a member of the Italian team that reached the final of UEFA Euro 2000, and he also represented his country at the 2002 FIFA World Cup.

After a season-long spell with Sampdoria, he was appointed Milan's manager in 2016, and later that year, he won his first title as a coach with the club, the Supercoppa Italiana.

Despite this, during the 1999–2000 season, Montella scored 18 goals, being the top scorer of the giallorossi, playing alongside Marco Delvecchio, in front of advanced playmaker Francesco Totti.

In January 2007, during the 2006–07 season, he was loaned to Fulham because Francesco Totti was the lone forward in new head coach Luciano Spalletti's 4–2–3–1 formation, while Montella wanted to have more chances to play.

[25] Montella quickly became popular with the Fulham fans, and showed his gratitude for making him feel at home at Craven Cottage.

[39] On 27 March 2002, he scored a notable double against England in an international friendly match in Leeds, giving Italy a 2–1 away victory after they had been trailing 1–0, with his second, match-winning goal coming from an injury-time penalty.

[48] Nicknamed "L'Aeroplanino" ("The Little Airplane"), due to his small stature and trademark goal celebration, in which he spread his arms like wings, Montella was known as a quick, hard-working, intelligent and opportunistic left-footed striker, who was gifted with pace, good technique and a keen eye for goal, and was capable of striking the ball well with either foot; he has also been described as a "fine all round player, with excellent passing and dribbling skills."

However, despite his ability and goalscoring record as a footballer, at times he was criticised by his Roma manager Fabio Capello for being a "selfish" player; he was also known to be injury-prone.

[54] On 21 February 2011, he was appointed as interim head coach of the first team for the remainder of the season, taking over the role from resigning boss Claudio Ranieri.

On 9 June 2011, and only a few days after being released by Roma, Montella was announced as new boss of Catania, signing a two-year contract with the Eastern Sicilian club.

[59] He led Catania to a mid-table placement, and ahead of Sicilian rivals Palermo for the first time in eight years; by the end of season, he was heavily linked with a comeback at Roma and the vacant job at Fiorentina.

[61] Montella's arrival saw a massive upheaval of the squad, which saw 17 (including Borja Valero and Alberto Aquilani) out of the 26 senior players being new to the club.

Fiorentina finished the 2012–13 Serie A in fourth place, missing out on a Champions League spot to Milan on the final day of the season.

In his third season, Montella helped Fiorentina reach the semi-final of the 2014–15 UEFA Europa League, where they were eliminated by defending champions and eventual winners Sevilla.

He signed a two-year deal, reportedly worth €2.3 million per year, while Sampdoria were paid €500,000 as a compensation to release him from his contract.

[67][68] On 23 December, Montella led the "Rossoneri" to their first title since 2011, the Supercoppa Italiana, defeating Juventus 4–3 in a penalty shootout, after a 1–1 draw following extra time.

[72] Although much was expected of Milan after a €200m summer transfer campaign financed by the team's new owners, the first half of the 2017–18 season was disappointing for the club; Montella drew criticism in the media for struggling to find a suitable formation for his players and a fixed starting eleven, and only won six out of the first 14 games in the league.

[76][77] On 28 December 2017, Spanish club Sevilla announced the appointment of Montella as the replacement of the recently-sacked Eduardo Berizzo, signing a contract which would last until mid-2019.

[78] During his tenure, Montella managed to guide Sevilla to a first-ever Champions League quarter-final, defeating Manchester United 2–1 on aggregate in the round of 16.

[82] Despite being the finalists of the Copa Del Rey, Sevilla struggled with their league form, and on 28 April 2018, Montella was sacked, following a run of nine games without a victory.