Inspired by his father to begin racing, Monteiro drove in the 1997 French Porsche Carrera Cup, taking five wins and five pole positions to become B-class champion and rookie of the year. In 1998, he entered French F3, finishing 12th overall and winning the rookie of the year award. He continued in 1999 with one win and three podiums to finish sixth. In 1999 he also competed in the Le Mans 24 Hours, finishing 17th overall and sixth in the GT2 class, and won the International Renault Finals at Estoril from pole with fastest lap.
In 2000, Monteiro finished second in French F3 after four wins, competed in the Formula 3 European Championship double-header, finishing second with a win at Spa-Francorchamps, and came second in the Korea Super Prix and ninth at the Macau Grand Prix. In 2001, he again finished second in French F3 with six poles, four wins and four podiums, and also competed in the French GT Championship.
In 2002, Monteiro stepped up to the F3000 Championship with Super Nova, achieving five top-ten finishes to rank 12th. He also completed the Renault F1 Driver Development Scheme and tested with the Renault team at Barcelona. In 2003, he joined Fittipaldi Dingman Racing for the Champ Car World Series, achieving a front-row start in Mexico City and leading two races, finishing 15th overall with 29 points.
Monteiro was signed as an official Minardi F1 test driver for 2004, but also competed in the Nissan World Series by Nissan with Carlin Motorsport, finishing second behind Heikki Kovalainen and winning Rookie of the Year.
After the Midland Group bought Jordan Grand Prix, Monteiro was announced as a full-time driver alongside Narain Karthikeyan for the 2005 season, debuting at the Australian Grand Prix.
At the 2005 United States Grand Prix, the Michelin-equipped teams withdrew from the race due to tyre safety concerns, leaving only the three Bridgestone-equipped teams to contest it. Monteiro finished third of the six remaining drivers, becoming the first Portuguese driver to achieve a Formula One podium. At the podium ceremony, where none of the scheduled dignitaries were present, Michael Schumacher and Rubens Barrichello accepted their awards and quickly exited; Monteiro stayed to celebrate alone, receiving applause from the fans.
By the 2005 Belgian Grand Prix, Monteiro had finished every race of the season, breaking the record for consecutive finishes for a rookie in Formula One, previously held by Jackie Stewart (1965) and Olivier Panis (1994). This record stood until 2013 when Max Chilton finished all 19 races. Shortly before the 2005 Turkish Grand Prix, his team principal Colin Kolles, a qualified dentist, performed emergency root canal surgery on Monteiro, enabling him to race.
In 2006, Monteiro was re-signed to partner Christijan Albers at the re-branded Midland. Their M16 car failed to score any points across 18 races; Monteiro retired six times and achieved a season-best ninth at the Hungarian Grand Prix. At the end of the year, the team was renamed Spyker and signed Adrian Sutil in Monteiro's place. Monteiro briefly held discussions about a Toro Rosso drive, but the team confirmed Vitantonio Liuzzi and Scott Speed, leaving him without a seat. He departed Formula One with one podium and seven championship points.
In March 2007, Monteiro joined the SEAT Sport team in the WTCC, driving a SEAT León. He made his debut at the second round at Zandvoort and finished the season 11th overall with three podiums and a pole position.
In 2008, driving the TDi version of the SEAT León, he took his first WTCC win at Puebla in Mexico and a further win at Estoril in Portugal, finishing 12th overall in a championship won by SEAT team-mate Yvan Muller, with SEAT also taking the manufacturers' title. In 2009, he scored two podiums in Valencia and Brno to finish ninth overall, again contributing to SEAT's manufacturers' championship. After SEAT announced withdrawal from the WTCC, Monteiro joined the SR-Sport team run by Sunred Engineering for 2010, alongside Gabriele Tarquini, Jordi Gene, and Tom Coronel. He won at Portimão and Valencia and finished fifth overall. He continued with Sunred into 2011 and 2012, the latter under the "Tuenti Racing Team" banner.
Monteiro joined the Honda Racing Team JAS from the 2012 Race of Japan, driving the new Honda Civic. He scored the first WTCC podium for the Civic at the 2012 Guia Race of Macau. For 2013, partnering Gabriele Tarquini, he took his first Honda WTCC win at Shanghai and scored five further podiums, helping Honda win the manufacturers' world championship.
In 2014, Monteiro scored five podiums and one pole position to finish fifth in the standings. In 2015, he won in Russia and in Japan. In 2016, he won in Slovakia and Portugal and finished third in the championship—his best result—behind José María López and Yvan Muller.
In 2017, Monteiro had taken two wins and five podiums and led the standings after 12 races when he sustained serious injuries in a testing crash caused by a brake failure at Barcelona in September, ending his season. In 2018, now in the re-branded World Touring Car Cup (WTCR), he was set to drive for Boutsen Ginion Racing in the FK8 Honda Civic Type R TCR but was not fully recovered from his injuries until returning at Suzuka for the penultimate round. He did not take part in the season finale at Macau on medical advice.
Monteiro made a full return in 2019 with KCMG, taking his first WTCR win since the accident at his home race in Portugal. He also won the Nürburgring 24 Hours in the TCR class in 2019 and 2020. He contested the final three seasons of the WTCR before the series collapsed at the end of 2022.
In October 2010, Monteiro competed as a guest driver in the Gold Coast 600 round of the V8 Supercar Championship Series at Surfers Paradise, sharing a Holden VE Commodore with Tony D'Alberto under the Centaur Racing banner. The pair recorded a DNF and a 17th-place finish.
In November 2008, Monteiro purchased the BCN Competición GP2 team and renamed it Ocean Racing Technology. The team competed in GP2, GP2 Asia Series, and GP3, including a 2009 Belgian feature race win with Portuguese driver Alvaro Parente. The team withdrew from GP2 and GP3 at the end of 2012 due to lack of funding. Monteiro manages the career of António Félix da Costa, who won the Formula E World Championship in 2019–20, and his son Noah.
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