During a 21-year professional career, he appeared in 346 Serie A games, most notably representing AC Milan (12 seasons) with which he won 12 major titles, including five national championships and the 1994 Champions League.

[2] After two more loans, Rossi returned to Cesena for the 1986–87 campaign, only missing five games as the Emilia-Romagna club promoted to Serie A, and retaining first-choice status in the following three top division seasons, with the team finishing 12th in 1989–90; he made his debut in the competition on 13 September 1987, in a home match against SSC Napoli.

[2] After his first season in Italy's top flight, Rossi was noticed by AC Milan, and joined the Rossoneri (also dubbed the Dream Team) that dominated Italian football for much of the 1990s.

[10] Under Sacchi, Rossi received two international call-ups by the end of 1994, but failed to make a single appearance for his country, although several pundits regarded him as a viable alternative to the then first-choice keeper Pagliuca;[11][12][13] he still managed to have a successful club career under the tutelage of Fabio Capello, as the Invincibles went on a 58-match unbeaten run and won four Scudetti in five seasons, as well as the UEFA Champions League in 1994.

[2][17][18][19][20] Due to his good reactions, agility, athleticism and solid positioning, he was also an effective shot-stopper, and, despite his height, was gifted acrobatically and capable of getting to ground quickly to parry shots, which made him adept at saving penalties.

[2][17][18][19][21] Despite his talent,[19][22] he was at times criticised for his volatile, arrogant and controversial character, however, which led him to pick up several cards throughout his career, as well as his tendency to commit occasional costly mistakes, which, along with his height and athleticism, earned him the nickname "l'ascensore umano" (the human lift).