Born in Santarcangelo di Romagna, the province of Rimini, Romagna region, Rossini started his professional career at Romagna club A.C. Cesena. In 2007–08 Serie B which the team eventually relegated, he played 5 times as understudy of Gianluca Berti and then Artur. That season he also played 3 times for the reserve. In 2008–09 season he moved down one level for Ivrea, which the first choice of Cesena was occupied by fellow youth product Nicola Ravaglia. Rossini was the first choice in 2008–09 Lega Pro Seconda Divisione for the Piedmontese club. However Ivrea folded at the end of season despite finished in the mid-table. Rossini's mother club Cesena promoted back to 2009–10 Serie B in 2009, that made both Ravaglia and Rossini once again left the club.
Rossini was signed by Foligno Calcio in co-ownership deal for a peppercorn of €500. Rossini was the starting keeper in both 2009–10 and 2010–11 Lega Pro Prima Divisione season. He was one of the protagonist to 2–2 draw with Pistoiese in relegation "play-out" (playoff) and survived from relegation due to better regular season result (35 points verse 33 pts.). In June 2011 Cesena bought back Rossini for €150,000 and signed a new 4-year contract. His previous contract was set to expire on 30 June 2012.
Rossini returned to Cesena in June 2011 but left for newly relegated third division club Frosinone Calcio on 5 August 2011 in temporary deal with 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.
In June 2012, few days before the closure of 2011–12 financial year of "AC Cesena SpA" and "Parma FC SpA", both club made notional swap deals, which also happened in June 2010 and 2011. Cesena got bomber Gianluca Lapadula for €1.4M and Gregoire Defrel for €1.2M (Rossini was Lapadula's teammate in Ivrea), and Parma signed Rossini for €1.6M and Nicola Del Pivo for €1M. All 4 players were signed in co-ownership deal. Cesena suffered from relegation from Serie A and the already needed re-capitalization in June 2011. Rossini signed a 5-year contract.
On 10 July 2012, he received a call-up to pre-season camp, but for Cesena. Despite Parma had sold Gasparri outright, sold Stefano Russo in co-ownership deal, loaned out Alberto Gallinetta on 7 July; Rossini still excluded from the squad of Parma (along with Alessandro Iacobucci) as Parma preferred Pavol Bajza (b. 1991) as third keeper and youngster Francesco Anacoura (b. 1994) as the fourth of the first team and the first choice of the reserve.
Nevertheless Rossini did not have a place in Cesena despite played once in the friendly, Rossini returned to fourth division for A.C. Bellaria Igea Marina in August. The co-ownership of Rossini was renewed in June 2013.
Rossini also received call-up to Cesena's pre-season camp for 2013–14 Serie B. He was the second keeper of the team, behind Andrea Campagnolo in the friendlies. However, Cesena did not award any shirt number to him. On the eve of 2013–14 Coppa Italia, Cesena finalized the loan deal of Rossini from Parma and awarded no.1 shirt to him. Rossini was the first choice in the first round of the cup but on the bench in the second round. Rossini lost his role as deputy in the first round of 2013–14 Serie B to new signing Achille Coser. Cesena also received €280,000 from Parma as premi di valorizzazione of the loan.
On 30 July 2014, Rossini was loaned out once again, this time to newly promoted Lega Pro club Lupa Roma. However Rossini became the deputy of Francesco Rossi. On 8 January 2015 Rossini was signed by Savona.
On 25 June 2015 Rossini became a free agent.
Rossini was signed by Reggiana on 19 August 2015. Rossini was the second-hand behind Simone Perilli.
Rossini received call-up from Italy national under-19 football team in September 2008 from Massimo Piscedda. Piscedda dropped Simone Colombi (born 1991), Carlo Pinsoglio and Sergio Viotti who all received a call-up for the first training camp. The aforementioned all made their U21 debut in the latter part of their career. In Moldova, which the 2009 UEFA European Under-19 Football Championship qualification Group 1 took place, Rossini beat Filippo Perucchini to become the first choice. Unfortunately Italy was eliminated as the third of the group. That season he also received call-up from Italy national under-20 football team coached by Francesco Rocca before and after he received his U19 call-up. Rossini entered the training camp in August 2009. The team (b. 1989 team) qualified to 2009 FIFA U-20 World Cup in September 2009 as 2008 U19 Euro runner-up, and Andrea Gasparri (b. 1989) and Antonio Piccolo (b. 1990) eventually beat other footballers to become the backup of Vincenzo Fiorillo (b. 1990, who back from U21 team) in the World Youth Cup.
Rossini failed to play any game in national level since October 2008, and eventually dropped from U20 A team. He received a call-up from Lega Pro U20 representative team in September 2009 for a training camp and again in June 2010 for 2010 Trofeo Dossena. In that tournament, the team beat Internacional youth side in the finals. Rossini was the first choice in all 5 matches and backed by Pasquale Pane. He also won 2010 Lega Pro Prima Divisione under-21 Tournament with the U21 side of Prima Division Group A (Third Division Group A) in January 2010. The two teams made 10 substitutes in total (6+4) at half time which Rossini was replaced by Luca Vino (b. 1991).