U21 Stroppa was coach of Milan's under-21 team for the 2010–11 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. Südtirol On 13 July 2011 he was unveiled as new head coach of Südtirol. Pescara 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. Spezia In June 2013, he was named new head coach of Serie B club Spezia. Return to Südtirol On 20 April 2015, Stroppa returned as head coach of Südtirol; ending the 2014–15 season in tenth place. The following season, Stroppa helped the side finish in tenth place once again. On 12 May 2016, Südtirol communicated that Stroppa's contract would not be renewed following its expiration on 30 June. Foggia On 14 August 2016, he was appointed by Foggia. He reached a promotion to Serie B with the Pugliese team. Crotone In June 2018, Stroppa was appointed as coach of Crotone, replacing Walter Zenga. Crotone announced the dismissal of Stroppa on 29 October 2018. He was reinstated as head coach on 28 December 2018, following the resignation of Massimo Oddo, who had previously replaced him in charge of the Calabrian club. Since his return at Crotone, Stroppa led the Calabrian club to twelfth place in his first season, and was awarded a new contract. On his second season, he led Crotone to automatic promotion to Serie A, leading the Rossoblu back to the top flight after a two-year absence. His debut season as a Serie A manager however did not prove to be successful, as Crotone struggled to stay out of the relegation zone, leading to Stroppa being sacked on 1 March 2021. Monza On 28 May 2021, it was announced that Stroppa would be appointed head coach of Monza on 1 July. He