Stewart's first competitive drive came under unusual circumstances. In 1973, he was scheduled to co-drive — act as navigator — in the Ensenada 300 in a Class 1-2 dune buggy. When his driver broke his leg before the race, Stewart took the wheel himself and won. That debut victory launched a professional racing career that would last more than a quarter century.
In 1983, Stewart joined the Toyota factory racing program, running under Cal Wells at Precision Preparation Inc. The alliance proved extraordinarily productive. Over the course of the partnership Stewart collected victories across the principal events of American desert and stadium off-road racing.
His Baja 1000 record includes three outright wins, and he holds the distinction of being the only driver to win the Baja 1000 overall — including motorcycles in the classification — while piloting a four-wheel vehicle solo. He won ten points championships in total: four SCORE World Championships and three Mickey Thompson Entertainment Group championships are among the headline titles.
In the MTEG stadium series, which brought off-road racing to purpose-built urban arenas, Stewart posted 17 wins — the all-time series record. His Baja 500 record of 17 wins is similarly unmatched. The 1993 season produced a landmark achievement when Team Toyota became the only manufacturer to sweep what are informally called the Crown Jewels of desert racing — the Nevada 500, the Baja 500, and the Baja 1000 — within a single season.
Stewart retired from competition in 1999.
After stepping away from the cockpit, Stewart co-founded the ProTruck Racing Organization (PRO), a spec series using identical chassis that competes as a class within major desert races including Best in the Desert's Vegas to Reno event. The organization built 45 trucks over its decade of operation.
In 2008, Toyota released a limited-edition "Ivan Stewart Ironman" variant of its Tundra pickup truck, featuring Toyota Racing Development wheels, grille, interior, and supercharger, along with a special signature package — a commercial acknowledgment of Stewart's role in the brand's off-road identity.
Stewart lent his name and racing style to a 1989 arcade video game, Ivan 'Ironman' Stewart's Super Off Road, which became a popular title and was subsequently ported to home gaming platforms. In 1997, a sequel, Off-Road Challenge, was released by Midway Home Entertainment, again drawing on his racing persona.
Beyond motorsport, Stewart wrote Ivan "Ironman" Stewart's Ultimate Off-Road Adventure Guide, published by Motorbooks in 2007. He has worked with the Special Olympics and the Make-A-Wish Foundation, and has supported a school for the deaf in Ensenada, Mexico, through fundraising activities.
Stewart was inducted into the Off-road Motorsports Hall of Fame in 2006. In 2009 he was inducted into the San Diego Hall of Champions Breitbard Hall of Fame. On March 17, 2020, he was inducted into the Motorsports Hall of Fame of America.
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