In 1993 he won both the Ballon d'Or and the FIFA World Player of the Year award, and is still remembered as one of the most beloved and technically gifted players in his country.

Born in Caldogno, near Vicenza, Baggio started his career with Vicenza in Serie C1 in 1981. Fiorentina snapped him up in 1985, and during his years there, he rose to cult status among the team's fans. He was sold to Juventus amid large fan outcry in 1990 for 15 billion Italian lira ($19 million), the world record transfer for a football player at the time. Baggio replied to his fans saying: "I was compelled to accept the transfer". That year he played in his first World Cup, and although he was used most often as a substitute in the 1990 tournament, he was still able to display his quality, scoring twice including the "goal of the tournament" against Czechoslovakia. In 1993 he won his lone European club trophy, helping Juventus to the UEFA Cup.

Roberto was the cornerstone of the Italian team during the 1994 World Cup, leading them to the final after a disappointing start. He scored five goals, all in the medal round: two in the Round of 16 to beat Nigeria (with a late equalizer and one in extra time), one in the quarter-finals to top Spain, and two to beat Bulgaria in the semifinals. Unfortunately, Baggio was not fully fit for the final against Brazil, and missed Italy's last penalty (Brazil still had a kick left) as the South Americans won the World Cup title after a 0-0 tie. Two other Italians, Franco Baresi and Daniele Massaro, had already missed penalties; had Baggio scored, Brazil would have still had a penalty to win the Cup nevertheless.