Montermini made his racing debut in a 1987 Formula Boxer race at Monza. He progressed to Formula 3 in 1989 with Euroteam, winning the final round of the Italian championship in a Reynard 893-Alfa Romeo and finishing second in the Monaco Formula 3 support race.
He moved to Formula 3000 for 1990, immediately qualifying on pole position for his debut at Donington Park in a Mansell Madgwick Reynard 90D-Mugen before crashing out after 12 laps. He scored podium finishes at Jerez (third) and Le Mans (second) but errors limited his results. In 1991, driving a Ralt RT23-Cosworth for 3001 International, he led at Pau before a gearbox failure and took pole at Hockenheim, finishing third on two occasions.
His 1992 campaign was the most successful of his F3000 years. He began the season with Il Barone Rampante in a Reynard 92D-Judd, taking pole at Pau and Barcelona and winning in Spain, before his funding ran out mid-season. Picked up by Forti Corse, he won two more rounds to finish championship runner-up, behind compatriot Luca Badoer.
Montermini first raced in North American open-wheel competition in 1993, contesting four Champ Car events for the underfunded Euromotorsport team in a Lola T92/00-Chevrolet. His best result was fourth place at Detroit. He started 1994 in the series again, this time with Dale Coyne Racing, before pivoting to Formula One mid-season.
He returned to American racing in 1999, driving four events for Dan Gurney's All American Racers team in the final season of Gurney's ownership, after Alex Barron, Gualter Salles, and Raul Boesel had all preceded him in the seat. His best result that season was eleventh place at Vancouver.
Montermini's Formula One career was shaped by circumstance and misfortune. He first attempted to qualify for an F1 race in Spain in 1994 while still part of the Champ Car circus, trying the Simtek S941 that had recently been driven by Roland Ratzenberger — who had been killed during qualifying for the San Marino Grand Prix earlier that season. He failed to qualify after crashing in practice.
He was formally signed by Simtek for the remainder of 1994 as Ratzenberger's replacement, making his World Championship debut at Barcelona. A heavy practice accident there broke his left heel and his right foot, ending the season before it had properly begun.
For 1995 he joined Pacific Grand Prix, normally qualifying outside the top twenty in a car without the resources to compete for points, though he recorded a career-best eighth place in Germany. In 1996 he moved to Forti Corse alongside fellow Italian Luca Badoer — a reunion of the duo who had dominated F3000 in 1992 — until Forti's financial situation forced the team to abandon the championship after the French Grand Prix.
From 2000 onwards Montermini rebuilt his career in endurance and GT competition. He raced at the 1998 24 Hours of Le Mans in a Nissan R390 GT1, finishing sixth in class, and returned to Le Mans in 1999 in a Courage C52, finishing sixth overall. He competed in the 2001 24 Hours of Daytona and established himself primarily in the FIA GT Championship driving Ferrari machinery, accumulating two class wins and four further class podiums.
In 2006 he shared a Zakspeed Racing Saleen S7R-Ford with Jarek Janis and Sascha Bert, winning the FIA GT race at the Hungaroring. He also won the GT Italia championship in 2010.
In the International GT Open his record was outstanding. He won the GTA class in 2007 driving a Ferrari 430 for Scuderia Playteam alongside Michele Maceratesi, then the pair went on to win the overall championship in 2008. Montermini added a second overall International GT Open title in 2013.
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