Rugolo began his motorsport career in karting in 1994 and was active until 1999 in this sport. In 2000 he moved to Formula racing and competed in the Italian Formula Renault. After he had occupied 20th overall in the first season, 2001, he was seventh in the overall standings. Rugolo 2002, even in a race the Italian Formula Renault part, but its main focus was on the Formula Nissan 2000, the Drivers' Championship, he was 13.
In 2003, the Italians in the sports car racing and was 14th in the SR1 - standings of the FIA Sports Car Championship. He also began a race championship at the Italian Super Production Car and finished in eleventh place in the LMP -900 rating in the 24- hour race at Le Mans.
2004 returned Rugolo back into formula racing and competed in the Italian Formula 3 Championship. Rugolo won a race and finished the season in fourth place in the championship. He also was the last race of the 2004 season his debut in the International Formula 3000 Championship. In Durango Corse he replaced his compatriot Matteo Meneghello and could not finish the race.
In 2005 he was again no cockpit in Formula racing and went instead to the American Le Mans Series ( ALMS). The Italian was seventh in the overall standings. He also took part in two races of the Italian GT Championship and both could decide for themselves. In 2006 he returned again to Formula racing and went away again in the Italian Formula 3 Championship at the start. This time Rugolo won two races and finished the season as two years earlier, in fourth place overall. In 2007 he took part in a half- season of the FIA GT Championship and was a podium placing 14th in the overall standings.
2008 Rugolo moved to the International GT Open and he won a race in the GTA rating. His first season he finished in ninth place overall. In 2009, he contested the season with Giacomo Ricci and was able to win a race. The two stood in half of all races on the podium and occupied the fifth place in the championship. In 2010 he replaces both the Italian GT Championship, as well as in the Superstars GTSprint.