[16] Under his guidance, Trapani concluded the 2018–19 season in second place behind champions Juve Stabia, and then successfully contested the playoff phase, winning promotion to Serie B after defeating Piacenza 2–0 on aggregate.

[21] In his first season in charge, Italiano led Fiorentina to win a spot for the 2022–23 UEFA Europa Conference League by finishing 7th in Serie A, thus marking a return into European football for the Viola after several years.

Their memorable campaign ended with a narrow 2–1 defeat to Premier League side West Ham United in the final minute of regulation time.

[36][37][38] Tactically, he used the 4–3–3 formation during his time as head coach of Spezia, with a deep-lying playmaker flanked by two box-to-box midfielders, or mezzali, who were capable of making late attacking runs off the ball.

His team was capable of defending either in a deep or mid-block, with a compact shape, restricting spaces for his opponents, while also incorporating aspects of man-to-man marking off the ball.

After winning back possession, his Spezia side were known for moving the ball quickly with their passing to initiate counter-attacks, and utilised the wings without resorting to traditional wing-play.

[43] While Italiano has earned praise in the media as promising manager,[40] he has also been criticised by certain pundits for his overly predictable possession-based style, and for his teams' inability to convert their chances or score many goals despite controlling the ball.

[37] Others have instead criticised him for his game-plans, as his Fiorentina side often lost game in seemingly preventable manners,[42] which has led the press to question his teams' mentality, in particular following their three consecutive final defeats between 2022 and 2024.