Born in Santarcangelo di Romagna, the province of Rimini, Emilia-Romagna, Rossini started his professional career at Romagna club A.C. Cesena. In the 2007–08 Serie B season, in which the team was relegated, he played five times as understudy of Gianluca Berti and later Artur; Rossini also played three times for the reserve. In the 2008–09 season he moved down one division to Ivrea; on loan as the first choice goalkeeper of Cesena was fellow youth-product Nicola Ravaglia. While on loan, Rossini was the first choice in 2008–09 Lega Pro Seconda Divisione for the Piedmontese club, but Ivrea folded at the end of season despite finishing mid-table. Rossini's parent club Cesena was promoted back to 2009–10 Serie B and both Ravaglia and Rossini left the club.
Foligno
Rossini was signed by Foligno Calcio in a co-ownership deal for €500. Rossini was the starting keeper in both 2009–10 and 2010–11 Lega Pro Prima Divisione seasons. He was one of the players in the 2–2 draw with Pistoiese relegation playoff and Foligno escaped relegation due to a better regular season result. In June 2011, Cesena bought back Rossini for €150,000 and he signed a four-year contract; his previous contract was set to expire on 30 June 2012.
Cesena and Frosinone
Rossini returned to Crecesena in June 2011 but left for newly relegated third-division club Frosinone Calcio on 5 August 2011, in a temporary deal with the club having the option to buy half of the registration rights. Rossini was the understudy of Emanuele Nordi and Massimo Zappino. In February 2012, after the closure of winter transfer window, Rossini was allowed to train with home-province club Rimini.
Parma
In June 2012, a few days before the closure of the 2011–12 financial year of "AC Cesena SpA" and "Parma FC SpA", both clubs made notional swap deals. Cesena received striker Gianluca Lapadula for €1.4 million and Grégoire Defrel for €1.2 million, and Parma signed Rossini for €1.6 million and Nicola Del Pivo for €1 million. All four players were signed in co-ownership deals; Rossini signed a five-year contract. On 10 July 2012, Rossini received a call-up to pre-season camp, but for Cesena. Although Parma had sold Andrea Gasparri outright, sold Stefano Russo in a co-ownership deal, and loaned out Alberto Gallinetta on 7 July, Rossini still was excluded from the first-team squad of Parma as Parma preferred Pavol Bajza as their third keeper and youngster Francesco Anacoura as the fourth choice of the first team.
Bellaria (loan)
Rossini did not have a place in Cesena despite playing once in a friendly, and he returned to the fourth-tier for A.C. Bellaria Igea Marina in August 2012. The co-ownership of Rossini was renewed in June 2013.
Cesena (loan)
Rossini also received a call-up to Cesena's pre-season camp for 2013–14 Serie B. He was the second-choice keeper of the team after Andrea Campagnolo in the friendlies. Cesena did not, however, assign any shirt number to him. On the eve of the 2013–14 Coppa Italia, Cesena finalised the loan deal of Rossini from Parma and awarded the number 1 shirt to him. Rossini was the first choice in the first round of the cup but remained on the bench in the second round. Rossini also lost his role as deputy in 2013–14 Serie B to new signing Achille Coser. Cesena received €280,000 from Parma as premi di valorizzazione of the loan.
On 30 July 2014, Rossini was loaned out again, this time to newly promoted Lega Pro club Lupa Roma where Rossini became the deputy of Francesco Rossi. On 8 January 2015, Rossini was signed by Savona and on 25 June 2015 Rossini became a free agent.
