Gavaggio was an alpine ski racer at the beginning of his sports career , but no major successes were achieved. He contested his last alpine ski race in March 1997, after which he switched to ski cross. He won the gold medal at the Winter X Games in 1999. He was never able to repeat this success in later years, finishing third six times.
Gavaggio made his debut in the Freestyle World Cup on November 30, 2002 in Tignes ; in the first ski cross world cup race in history, he finished 6th. He celebrated his first victory on January 18, 2003 in Laax . At the end of the season he was second in the discipline classification. During the 2003/04 World Cup season, Gavaggio was able to win three more races, in the discipline classification he again only missed victory by a few points. After not getting past fourth place in winter 2004/05, he achieved his fifth (and final) World Cup victory in February 2006.
In the 2006/07 season Gavaggio did not take part in the World Cup, but entered the World Championships in Madonna di Campiglio in March 2007 and won the bronze medal there. In 2008 he again achieved a World Cup podium, after which he increasingly found it difficult to keep himself in the top of the world. Nonetheless, Gavaggio qualified for the 2010 Winter Olympics : He finished fifth in Cypress Mountain and resigned immediately after the Olympic race.