Di Biagio began to achieve greater international exposure and fame in Italy due to his excellent and consistent performances whilst playing for Roma (1995–99), where he remained for five seasons, under managers Carlo Mazzone, Carlos Bianchi, and Zeman once again; he would make his career debut in European Competitions with the club. During his time at Roma, he was able to help the squad to a fourth-place finish during the 1997–98 season, and managed to subsequently reach the quarter-finals of the 1998–99 UEFA Cup and the 1997–98 Coppa Italia. His consistent performances led him to become a permanent member of the Italian national side during this period. Di Biagio would make 140 appearances for Roma in all competitions, scoring 18 goals. 15 of his goals were scored in Serie A in 114 appearances.