Boscoscuro began his riding career at the grand prix level in the 250cc class, where he demonstrated sufficient pace to become the 1995 250cc European Champion. His best season in the FIM Road Racing World Championship came in 1996, when he finished tenth in the 250cc class and won the IRTA Cup, the world championship award for the leading private team. After his riding career concluded, he transitioned into team management and sports direction, maintaining a continuous connection to the paddock.
In 2002, Boscoscuro joined Gilera and Derbi as Sport Director, a role he held until 2005. From 2006 to 2009 he served as team manager at Gilera, a period that culminated in one of the most celebrated outcomes of his career: in 2008, the Gilera team won the 250cc World Championship with Marco Simoncelli. The title confirmed Boscoscuro's ability to build and run a competitive programme around a talented rider, and Simoncelli's subsequent rise to MotoGP made the achievement all the more significant in retrospect.
In 2010, Boscoscuro launched an entirely new project with the founding of the Speed Up team, entering the newly created Moto2 class. The transition from two-stroke 250cc machinery to four-stroke 600cc engines that year required every team to adapt rapidly, and Speed Up responded with their own in-house chassis, the Speed Up S10. In the team's debut Moto2 season, the S10 secured six pole positions, three race victories, and nine podium finishes — a remarkable debut for a new constructor. Speed Up also became the only team in that inaugural season to place both riders on the podium in the same race.
In 2011, a change of frame supplier led to a more difficult campaign, with only two podium finishes across the season. Boscoscuro responded by co-founding Speed Up Factory in 2012 with Eros Braconi. The new entity developed the S12 chassis, manufactured entirely in Italy from design through to production. By 2013, the S12 attracted three external teams — NGM Mobile Forward Racing, QMMF Racing Team, and Arginano y Gines Racing Team — bringing the total to eight riders competing with the SF13 in the Moto2 class.
Boscoscuro's career represents an unusual trajectory in professional motorsport: a rider who became a constructive force in the same championship he once competed in. By establishing Speed Up as a competitive chassis manufacturer in Moto2, he moved beyond conventional team management into the technical domain of designing and selling frames to rival teams. His work with Marco Simoncelli at Gilera and the early success of Speed Up in Moto2 are the two most prominent markers of a career shaped by sustained commitment to the technical and competitive development of smaller-class grand prix racing.