Described as a "modern" footballer, Di Gennaro was a quick, agile, versatile and well-rounded player, with good
dribbling skills, who was known for his ability to adapt to different playing situations on the pitch, and was therefore capable of playing in several midfield positions. 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. In addition to his footballing ability, he was known for his leadership and humorous personality. ==After retirement==