Cairoli began racing in single-seaters in 2012, entering the Italian Formula Renault Championship and scoring one podium in the final four rounds of the season. He spent 2013 in the German Formula Three Championship before joining GSK Grand Prix for the 2014 Formula Renault 2.0 Alps Series, where he competed only in the opening round at Imola before departing.
Cairoli's move into sports cars in 2014 proved transformative. Joining Antonelli Motorsport in the Porsche Carrera Cup Italia, he dominated the series, winning six of fourteen races and taking the title by a margin of 70 points. The championship victory brought an invitation to compete for the Porsche International Cup Scholarship, which he won, earning €200,000 and Porsche Junior driver status for 2015.
As a Porsche Junior in 2015, Cairoli competed in both the Porsche Supercup and Porsche Carrera Cup Germany with Project 1 Motorsport. A second-place finish in the 2016 Porsche Supercup points standings earned him promotion to Porsche Young Professional status within the manufacturer's driver development hierarchy.
In 2017, Cairoli stepped up to the FIA World Endurance Championship, joining Dempsey-Proton Racing in the LMGTE Am class. His first appearance at the 24 Hours of Le Mans came that year, with the team finishing sixth in class. Over the full 2017 season, Dempsey-Proton finished second in the LMGTE Am standings, scoring class victories at the Nürburgring and in Mexico City. Cairoli also contested the European Le Mans Series with the team that year, taking a class win at Portimão as the team finished third in the championship.
Ahead of the 2019–20 FIA World Endurance Championship superseason, Cairoli returned to Team Project 1 for WEC duties.
In February 2020, Cairoli signed with Dinamic Motorsport to compete in the GT World Challenge Europe Endurance Cup. His most prominent result from the Porsche era came in 2021, when he was part of the Manthey Racing crew that claimed overall victory at the 24 Hours of Nürburgring, sharing the winning car with Kévin Estre and Michael Christensen.
At the 2023 24 Hours of Spa, Cairoli secured pole position, adding another notable milestone to his Porsche career. He departed the Porsche factory roster at the end of 2023 after nearly a decade within the manufacturer's programme.
For 2024, Cairoli joined the Lamborghini factory roster, contesting the IMSA SportsCar Championship with both the GTD Lamborghini Huracán and the GTP Lamborghini SC63 entries, and making another appearance at the 24 Hours of Le Mans. He left Lamborghini in January 2025 and joined Iron Lynx for the 2025 FIA World Endurance Championship.
Cairoli subsequently moved to the Deutsche Tourenwagen Masters, where he competes with Emil Frey Racing in a Ferrari 296 GT3 Evo.
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