Carobbi had three separate spells with Fiorentina throughout his career. Despite competition from legendary defenders such as Maldini, Baresi, Costacurta and Tassotti, he also played two seasons (1989–91) with A.C. Milan, winning the 1990 European Cup, two European Super Cups, and two Intercontinental Cups during an extremely successful period in the club's history under manager Arrigo Sacchi. He also played for Lecce.