Castiglioni started at international junior championships in 1998 and achieved his first major success at the 2000 European junior championship in Umhausen , when he won the bronze medal in the single-seater behind Elmar Leitner and David Mair . In the same year he also took part in a world championship in the general class for the first time and finished tenth. In 2001 he did not take part in the World Cup. Castiglioni contested his first World Cup race , which he finished in twelfth position, on January 24, 1999 in Canale d'Agordo . During the next two years, however, he did not make any further World Cup appearances.
From the 2001/2002 season , Castiglioni was back in the World Cup. He reached four top 10 places and ended up in tenth place in the overall World Cup. The worst result of the season he achieved at the 2002 European Championship in Frantschach , where he only came in 16th. For this he became Italian single-seater champion in 2002. In the 2002/2003 World Cup season , Castiglioni was among the top ten in all six races and achieved fifth place in Moscow as the best result , placing him ninth in the overall World Cup. At the 2003 World Cup in Železniki , he finished tenth.
The 2003/2004 World Cup season was Castiglioni's most successful. With two second places in the first and last races, he achieved his only podium finishes and with another three top 10 results he reached fifth place in the overall World Cup. In the 2004 European Championship in Hüttau Castiglioni won the silver medal, as well as in the World Cup in 2005 in Latsch . In the World Cup he did not achieve the results of the previous year in the 2004/2005 season . He only contested three World Cup races, in which he was only once in the top 5, and fell back to 14th place in the overall standings.
From the 2005/2006 season , Castiglioni only took part in a few World Cup races, but was mostly able to classify himself among the top ten. He contested his last World Cup race on January 31, 2009 in Deutschnofen . He started more and more in the Intercontinental Cup, won the overall ranking in the 2006/2007 season and came third overall in the 2009/2010 season. At the 2006 European Championships in Umhausen , Castiglioni was fifth. His next and last major event was the 2009 World Cup in Moos in Passeier , where he finished eighth. In 2010 Castiglioni ended his career.