Orsolini is a product of Ascoli's youth academy. He made his debut with the first team in the 2015–16 season in Serie B, obtaining 9 appearances in the league.
Juventus
On 30 January 2017, Orsolini joined Juventus on a contract until June 2021, for a fee of €6 million, plus an extra €4 million depending on certain conditions.[2] However Orsolini remained in Ascoli Piceno until the end of the season.
On 14 July 2017, Orsolini joined Atalanta on a two-year loan.[3]
Bologna
Orsolini moved back to Juventus and then on loan to Bologna in January 2018 after making only substitute appearances for Atalanta. The loan was for 18 months with an option to buy.[4] On 19 June 2019, Orsolini signed a deal with Bologna and signed for the club on a permanent basis.[5]
On 25 August 2023, Orsolini extended his contract with Bologna until 30 June 2027.[6][7]
International career
With the Italy U-20 side, Orsolini took part at the 2017 FIFA U-20 World Cup, and led the tournament in goals, scoring five, as Italy finished the competition in third place, their best ever result.[8][9] Due to his prolific performances, he was named by many in the media as the outright best player on the Italian side.[10]
He made his debut with the Italy U21 team on 1 September 2017, under manager Luigi Di Biagio, in a 3–0 friendly defeat against Spain.
Orsolini made his senior international debut for Italy on 18 November 2019, under manager Roberto Mancini, coming on as a substitute for Nicolò Barella in a 9–1 home win over Armenia, in Italy's final Euro 2020 qualifier; he marked the occasion by scoring his first international goal, and also later provided an assist for Federico Chiesa's goal.[11]
Style of play
Orsolini is a physically strong and fast-paced winger, who excels in one on one situations due to his excellent dribbling ability. Although he is naturally left-footed, he prefers to play on the right flank, in either a 4–3–3 or 4–2–3–1 formation, a position which allows him to cut into the centre and shoot on goal with his stronger foot.[12][13][14]