Bertolini began karting at the age of 11, progressing through the Italian karting ladder and finishing second in the Italian Championship. He won championships at national level and placed second in the Italian 125 Championship in 2000. His talent attracted Ferrari's attention at a remarkably young age: he became the youngest driver ever to serve as a Ferrari test driver at 19, later working in the experimental and development department.
In 2001, Bertolini made his GT racing debut driving a Porsche 996 GT3-R for Art Engineering in the NGT class of the FIA GT Championship. He joined JMB Racing in 2002, piloting a Ferrari 360 Modena through the 2002 and 2003 seasons and finishing fourth overall in 2003.
In 2004, Bertolini moved to Giesse Squadra Corse, again driving a Ferrari 360 Modena, finishing second overall and earning the "Driver Performance of the Year" award. His trajectory changed dramatically mid-season when he was offered a position on the Maserati AF Corse team to drive their newly developed GT1-class Maserati MC12 — a car Bertolini himself had helped develop. He accepted and won two races that year, at Oschersleben in Germany and Zhuhai in China, alongside teammate and former Formula One driver Mika Salo.
In 2005, Bertolini returned to JMB Racing with an MC12, finishing the season tied fourth. He also campaigned the MC12 in the American Le Mans Series that year, though without podium success, including a retirement at Mazda Raceway Laguna Seca.
For 2006, Bertolini joined the Vitaphone Racing Team, pairing with Michael Bartels in a Maserati MC12. The partnership was immediately successful: Bartels and Bertolini won the FIA GT Championship in the overall driver standings and led their team to the team championship title as well. The duo repeated the feat in 2008, 2009, and 2010, giving Bertolini three FIA GT Championship titles in total. He also claimed the inaugural FIA GT1 World Championship, making him the first champion of that series.
In 2011, Bertolini won the International Superstars Series driving a Maserati Quattroporte for Swiss Team. That year he also became the first driver to pilot Ferrari's new F1 Simulator at a ceremony held at Maranello.
From 2012, Bertolini competed in the FIA World Endurance Championship under the AF Corse banner, driving a Ferrari 458 Italia GTE alongside Olivier Beretta. His WEC campaign culminated in 2015 when he won the GTE Am class championship and, in the same season, claimed class victory at the 24 Hours of Le Mans in GTE Am — the pinnacle of endurance racing.
Bertolini continued to serve as the official test driver for Maserati, contributing to the marque's technical development alongside his racing commitments.
Bertolini's career is defined by an unusually close relationship with two of Italy's most celebrated automotive marques. His development work on the Maserati MC12 from the drawing board through to championship victory gave him a rare dual identity as both engineer-test driver and race winner. Three FIA GT Championship titles, the inaugural FIA GT1 World Championship, and a Le Mans GTE Am victory in 2015 place him among the most successful Italian GT drivers of the 2000s and 2010s.
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