Stringara started his career in the youth ranks of Inter Milan, then making his professional debut in 1980 with Siena.
He returned at Inter in 1990, being part of the Nerazzurri squad that won the 1990–91 UEFA Cup.
After more Serie C jobs, the last of which in 2015 at Grosseto, Stringara accepted an offer from friend and former teammate Jürgen Klinsmann to work alongside him in charge of the United States national soccer team.
[1] On 16 November 2021, Stringara returned into management as the new head coach of Serie D amateurs Pro Livorno.
[2] He was dismissed on 17 March 2022, leaving Pro Livorno dead last in the league table.