[2] During his club career, Di Gennaro played for Fiorentina (1976–80), Perugia (1980–81), Hellas Verona (1981–88) and Bari (1988–91).
[2] He made his professional debut with his hometown club Fiorentina at the age of 18, although, despite his talent, he struggled to find space in the club due to the presence of the team's star playmaker Giancarlo Antognoni, with whom Di Gennaro faced competition for a starting spot as the two did not play well alongside each other.
[1][9] He made his international debut on 3 November 1984, in a 1–1 draw against Switzerland, and all 15 of his caps were won whilst he was playing his club football with Verona.
He stood out throughout his career for his pace work-rate, stamina, defensive skills, and ball winning abilities, as well as his creativity and offensive capabilities in midfield; due to his wide range of skills, he was capable of playing both as a defensive midfielder, or in the centre as a deep-lying playmaker, courtesy of his vision, technique, range of passing and strong mentality, which enabled him to start attacking plays or distribute the ball quickly to his teammates after winning back possession.
Although he was mainly a team-player, he also had an ability to get forward, and was a powerful and accurate striker of the ball, and could also function as an advanced playmaker.