A year after signing for Milan, at the age of 24, Lentini was involved in a serious car crash whilst driving home from a pre-season tournament in Genoa, in August 1993. He fractured his skull and damaged his eye socket and he spent about two days in a light coma. After the crash he never fully recovered his mercurial dribbling skills. Plagued by 'memory loss', periods of blurred vision, and 'dizzy spells' he was tormented by the spectre of what his career once was, when he returned to the pitch at the end of the 1993–94 season. His teammate at the time, Marcel Desailly, was compelled to confess that “You could see the skills, how he was before the accident and after the accident, the balance was completely different”. His career in Milan fizzled out and culminated in a European Cup medal and another Serie A title that season, but this was merely for filling the bench; a paltry return for the world's most expensive signing at the time. The next two seasons would see him make few appearances, although he collected another Italian Supercup with the club, as well as a UEFA Super Cup, in 1994, also receiving runners-up medals in the 1994 Intercontinental Cup and the 1995 UEFA Champions League Final. During his final season with the club, he won a third Serie A medal.