Massimiliano Benassi (born 11 November 1981) is a former Italian association footballer who played as a goalkeeper.
Benassi played in Italian third category (Serie c1-c2, now called "Prima Divisione" and "Seconda Divisione"), and later joined the promotion in "Serie B" with U.S. Sassuolo Calcio in 2008. Then he played on good levels with Perugia Calcio.
On 28 June 2011 he extended his contract with Lecce for one more year.