Alessi began competitive racing in the Italian Touring Car Championship, where he became a consistent frontrunner. Between 1996 and 1999, and again in 2001 and 2002, he accumulated 12 pole positions and 12 race victories in the ITCC. These results established him as one of the leading figures in Italian tin-top racing during that era.
From 2003 to 2006, Alessi competed in the Trofeo Maserati Europe. Across four seasons he took 19 pole positions and won three races in the single-marque series. During the same period he also made three starts in the FIA GT Championship for Autorlando Porsche. The Maserati programme gave him significant experience in high-performance GT machinery under competitive, controlled conditions and served as a bridge to international GT3 racing.
Alessi joined the FIA GT3 European Championship in 2006, beginning with a Maserati Grand Sport. He progressed through a variety of cars over the following seasons: an Aston Martin DBRS9, a Corvette Z06, and a Ferrari 430 Scuderia. His most competitive FIA GT3 season came in 2007, when he finished third overall in the drivers' standings, accompanied by one pole position and two race victories. He continued in the series through 2010.
In 2008, while maintaining his European programme, Alessi competed in the Rolex Sports Car Series in North America. He drove a Pontiac GTO.R for Matt Connolly Motorsports P1 Groupe, sharing duties with Ryan Phinny during the season. For the 24 Hours of Daytona that year, the car was joined by Hal Prewitt, Karl Reindler, Vic Rice, and Spencer Trenery. He earned three podium finishes across the season, at Mid-Ohio, Montreal, and New Jersey Motorsports Park.
Alessi joined the ADAC GT Masters in 2011 with Callaway Competition, piloting a Callaway Corvette Z06. He became one of the defining figures of the series across five seasons:
In 2012, he finished second in the overall standings, his best result to that point.
In 2013, paired with Daniel Keilwitz, Alessi claimed the ADAC GT Masters drivers' championship. It was the title that defined his European GT career, achieved with the full support of the Callaway Competition factory programme. He remained with the team through 2015. Across his five ADAC GT Masters seasons, he accumulated five pole positions and eight race victories.
Alongside his sprint-racing commitments, Alessi built a substantial endurance record. He started the 24 Hours of Spa four times, made three starts at the 24 Hours of Daytona, completed two entries each at the Interlagos Thousandmiles and the 24 Hours of Sicily, and raced once in the Dubai 24 Hour. Across all endurance appearances combined he achieved four podium finishes globally.
Alessi's career spans the full width of Italian and international GT competition: from domestic touring cars in the ITCC, through the Maserati factory support programme and the FIA GT3 European Championship, to the ADAC GT Masters title with Callaway and Keilwitz. His 12 ITCC wins, 19 Trofeo Maserati poles, and 2013 ADAC GT Masters championship stand as the defining pillars of a long professional career in GT racing.
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