Career
Player
Milan
Union of European Football Associations Supercup: 1989, 1990, 1994
Intercontinental Cup: 1989, 1990
European Cup: 1989-1990
Supercoppa Italiana: 1994
Coach
Stroppa was coach of Air Corps Milan"s Primavera (under 21) team for the 2010-2011 season but was relieved of his duties on 11 June 2011, with a year still to run on his contract, and just one week after losing 1–0 to Roma in the quarter-finals of the Campionato Primavera. On 13 July 2011 he was unveiled as new head coach of Südtirol. On 8 June 2012, he was named head coach of Serie A newcomers Pescara, replacing Zdeněk Zeman, his former boss during his first spell as a player at Foggia, who was signed by Roma a few days before his appointment.
He was assisted by Andrea Guerra, Francesco Sità, Andrea Tonelli and Massimo Marini.
He resigned as coach of Pescara on 18 November 2012 after a series of bad results and the team has fallen in the middle of the relegation zone. He left the club along with Guerra (vice-coach) and two assistants Sità and Tonelli.
On June 2013, he was named new head coach of Serie B club Spezia. A quick, energetic, talented, yet injury-prone player, Stroppa was mainly known for his technical skills, and his ability to create chances for team-mates, which enabled him to play in several creative midfield and attacking roles: he was initially deployed as an attacking midfielder, or as a supporting striker, but he was also used as a winger, and even as a central midfielder on occasion.
He later played as a deep-lying playmaker during the final seasons of his career.