Rugolo began karting in 1992 and competed in kart championships through 1999. He then raced in Formula Renault 2000 Italy from 2000 to 2002, switching to Formula Nissan partway through 2002.
Rugolo competed in Italian Formula Three alongside his sports car programme, finishing fourth in the championship in both 2004 and 2006. His connection with the Durango operation, which also ran a Formula 3000 programme, earned him a single call-up to the International Formula 3000 series for the final round of the 2004 season at Monza; he retired from that race. Rugolo was listed among the drivers for A1 Team Italy in the 2006–07 A1 Grand Prix season, though his race appearances went to Enrico Toccacelo and Alessandro Pier Guidi.
Rugolo made his 24 Hours of Le Mans debut in 2003, finishing 24th overall in a Durango-Judd in the LMP900 class, co-driven by Sylvain Boulay and Jean-Bernard Bouvet. In 2005 he competed in the American Le Mans Series driving a Dodge Viper GTS-R. He entered the GT2 class of the FIA GT Championship in 2007 and moved to the International GT Open the following year.
The most prominent phase of Rugolo's career came in 2011, when he joined Krohn Racing for the team's Intercontinental Le Mans Cup campaign in the GTE-Am class, partnered with team owner Tracy Krohn and Niclas Jönsson. The trio won their class at the 12 Hours of Sebring and Petit Le Mans and finished second in the GTE-Am class championship. Rugolo returned to Krohn Racing in 2012 for the FIA World Endurance Championship, and continued with the team through the 2012 season at Le Mans, where he and his co-drivers finished third in class.
In 2014 Rugolo joined AF Corse for both the FIA World Endurance Championship and the United SportsCar Championship. At the 2014 24 Hours of Le Mans he co-drove with Stephen Wyatt and Sam Bird, though the car retired from the race. In the WEC that season the crew took a class pole at Silverstone and finished seventh in the GTE-Am standings.
In 2017 Rugolo was called into service under unusual circumstances: on the Wednesday before the 24 Hours of Le Mans, Lucas di Grassi was ruled out due to an ankle injury that prevented him from exiting the car quickly enough. Rugolo stepped in at short notice to replace him in AF Corse's Ferrari 488 GTE alongside James Calado and Alessandro Pier Guidi, finishing 46th overall in the GTE Pro class.
Rugolo has continued to compete actively in Italian GT competition and international GT events. Through early 2026 he remained active in the Italian GT Championship in the GT3 Am class. Over his career he has started more than 300 races and scored more than 30 wins and 85 podiums across all categories according to compiled statistics.