Born in Italy, Ascanelli embarked on his racing career in 1985 as a calculation engineer at Ferrari, a role he held for two years before transitioning to Fiat's rallying program with Abarth, where he worked as an on-event engineer. However, his stint with Abarth was short-lived, as he returned to Ferrari by the end of the year, this time as Gerhard Berger's race engineer, a position he held for three seasons until Berger left Ferrari to join McLaren.
Following Berger's departure, Ascanelli was taken to Benetton by his former Ferrari boss John Barnard, where he worked as an engineer for Nelson Piquet for two seasons. After Barnard's departure and Piquet's decision to retire from Grand Prix racing, Ascanelli joined McLaren for the 1992 season at the request of Gerhard Berger, with whom he had previously worked at Ferrari. During his time at McLaren, he collaborated with Berger's teammate Ayrton Senna, resulting in some of Senna's most notable victories in the 1993 season.
When Senna moved to Williams in 1994, Ascanelli did not remain at McLaren for long and returned to Italy in 1995 to work with Berger and Barnard once again. He eventually became the head of on-track engineering at Ferrari, overseeing both Berger and Jean Alesi. He held this position until the start of 1998, when it was announced that he would no longer be traveling to races that year, his job being taken by Ross Brawn. Ascanelli was rumored to be seeking a new opportunity but ultimately decided to remain with Ferrari under the new regime.
After a period in charge of research and development at Ferrari, Ascanelli moved on to Maserati, where he headed the competition department before returning to F1 with Scuderia Toro Rosso. During his time at Toro Rosso, he oversaw Sebastian Vettel's remarkable victory in the 2008 Italian GP. Currently, Ascanelli serves as the technical head of Brembo, a supplier of Formula 1 brakes.