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.