Born and educated in Italy, Ascanelli began his racing career in 1985 as a calculation engineer at Ferrari. After two years of number-crunching he moved across to Fiat's rallying program with Abarth, working as an on-event engineer but by the end of the year he had returned to Ferrari and began working as Gerhard Berger's race engineer. It was the start of a relationship which lasted for three seasons before Berger left Ferrari to join McLaren.

When Senna moved to Williams in 1994 Ascanelli did not last long at McLaren and went back to Italy in 1995 to work with Berger and Barnard again. He became head of on-track engineering at Ferrari, overseeing both Berger and Jean Alesi. He remained in that role until the start of 1998 when it was announced that he would not be traveling to races that year, his job being taken by Ross Brawn. Ascanelli was rumored to be looking for another job but stayed with Ferrari under the new regime. After a period in charge of research and development at Ferrari he is now involved in the technical liaison between Ferrari and Prost Grand Prix.He then moved to Maserati where he headed the competition department before returning to F1 with Scuderia Toro Rosso, where he oversaw Sebastian Vettel's extraordinary victory in the 2008 Italian GP. He is currently the technical head of Brembo, a supplier of Formula 1 brakes.