Stewart grew up in Bixby, Oklahoma, and began racing quarter midgets at the age of seven. He transitioned to sprint cars at age 16 under the guidance of veteran driver Andy Hillenburg. His early development in open-wheel short-track racing gave him a versatile foundation that served him across multiple sprint car disciplines throughout his career.
Stewart made his first World of Outlaws Sprint Car Series appearances in 1995 before going full-time in the series in 2005, earning the series Rookie of the Year title. He ran the full schedule again in 2008 for Roth Motorsports.
In 2014, Stewart joined the newly formed Larson Marks Racing — later known as Kyle Larson Racing — which became the most productive chapter of his career. Over five seasons with that organization, he won 35 feature events across multiple series. His finest single result came in 2015, when he won the Kings Royal at Eldora Speedway, one of the most prestigious events in sprint car racing. That same year he finished second in the overall World of Outlaws points standings behind Donny Schatz, the best series-championship result of his career.
In 2019, Stewart moved to CJB Motorsports, replacing David Gravel. He won the series special event at Nashville's Fairgrounds Speedway during that campaign but departed the team at the end of the season.
Alongside his World of Outlaws commitments, Stewart built an exceptional record in 360-cubic-inch sprint car competition. He won the Northwest Sprint Challenge Speedweek championship in 2007. He then claimed the American Sprint Car Series national touring title in 2009 and repeated the feat in 2011, winning that year's title by a single point over Johnny Herrera. Stewart won the Knoxville 360 Nationals five times and captured the Canadian Sprint Car Nationals three times, tying Steve Poirier for the most victories in that event. The National Sprint Car Hall of Fame and Museum named him 360 Sprint Car Driver of the Year in both 2009 and 2011.
Following his departure from CJB Motorsports, Stewart contemplated retirement but chose to return. He signed to run ten events with Roth Motorsports for the 2020 season, though those races were cancelled due to the COVID-19 pandemic. He subsequently ran the majority of the 2020 World of Outlaws season in the No. 71 car owned by Bernie Stuebgen. He won with that team at Williams Grove Speedway in the track's prestigious Summer Nationals and added another victory at Lakeside Speedway in October, the latter coming while substituting for David Gravel — who was competing in NASCAR Gander Outdoors Truck Series events — in Jason Johnson Racing equipment.
In the winter of 2016, between seasons, Stewart also won the off-season Winter Heat Sprint Car Showdown championship at Cocopah Speedway in Arizona.
At the conclusion of the 2020 season, Stewart announced his retirement from active competition. Rather than simply stepping away from racing altogether, he purchased Port City Raceway in his home state of Oklahoma to promote events there, maintaining a connection to the sport in an ownership and promotional capacity.
Stewart's career encapsulates the dual-discipline demands of elite sprint car racing, where success in both the 360 and 410 classes defines a driver's all-around ability. His back-to-back ASCS national titles, five Knoxville 360 Nationals victories, and a Kings Royal win place him among the more accomplished sprint car campaigners of his generation. His partnership with Kyle Larson's team during the mid-2010s coincided with a productive era for both driver and organization, producing consistent wins on the national tour.