Massimo Orlando (born 26 May 1971) is an Italian professional football coach and a former player, who played as a midfielder. He manages the youth team of ACF Fiorentina.

Orlando was born in San Donà di Piave. After beginning his club career with Conegliano Calcio (1986–1988), he played for seven seasons (122 games, 16 goals) in the Serie A, for ACF Fiorentina (1990–97) winning the Serie B in the 1993–94 season, A.C. Milan (1994–95) and Atalanta B.C. (1997–99); he played for Juventus in 1990 without making an appearance in Serie A for the club during the 1990–91 season. He also played for Reggina (1988–90), and retired in 2001, after a spell with Pistoiese.^[1]

At international level, Orlando was a member of the Italy U21 national team that won the UEFA European Under-21 Football Championship under manager Cesare Maldini in 1992.^[1]

Regarded as a promising player in his youth, Orlando was a creative and technically gifted attacking midfielder, with an excellent left foot and good dribbling skills. Although he was usually deployed in the centre, he was also capable of playing on the left. A team-player, although he was not a prolific goalscorer, he was known for his generous and unselfish playing style in midfield. Despite his talent, he struggled to live up to his potential and his career was also affected by several injuries.^[1]

Fiorentina

• Coppa Italia: 1995–96
• Supercoppa Italiana: 1996 (on the roster, but not played in the game)

Milan

• Supercoppa Italiana: 1994 (both times on the roster, but not played in the game)
• UEFA Super Cup: 1994 (on the roster, but not played in the game)

Italy U21

• UEFA European Under-21 Football Championship: 1992