Swindell began racing at age five in go-karts in Memphis, Tennessee. He won multiple junior karting championships through the late 1990s and early 2000s, capturing the World Karting Association Grand National Championship title in 2002 and back-to-back Tulsa Shootout Jr. II titles. He moved into quarter midgets in 1999, winning four national events, and soon transitioned into USAC and World of Outlaws competition.
Swindell made an immediate mark in dirt racing. At fifteen he became the youngest driver to finish in the top ten in a World of Outlaws Sprint Car feature, placing sixth at Parramatta in 2005. The following year, at seventeen, he became the youngest winner in World of Outlaws history when he took the checkered flag at Charlotte Motor Speedway's dirt track.
In 2007, Swindell joined forces with NASCAR driver Kasey Kahne to run the full USAC midget and sprint car schedule, finishing sixth and eighth in points in the two series respectively. He won the USAC Western World Championship at Manzanita in 2008 and claimed the 2008-09 Australian National Midget Championship — in Australia, midgets are called Speedcars — at the Murray Bridge Speedway.
His crowning achievement in dirt racing came at the Chili Bowl Nationals, the premier indoor midget race held each January in Tulsa, Oklahoma. Swindell won the event in 2010 at twenty years old, becoming the youngest champion in the race's history. He successfully defended in 2011 and 2012, and in January 2013 he became the first driver ever to win four consecutive Chili Bowl Nationals, a record that defined his legacy in the sport. Over his career he accumulated 77 victories across various dirt racing series, including the USAC Knoxville Nationals and the Louis Vermeil Classic.
Swindell made his stock car debut in the ARCA Racing Series at Salem in 2006. He expanded into the NASCAR K&N Pro Series East in 2008 and ran the full 2010 schedule, scoring two poles, one top-five, and four top-tens. He made his NASCAR Nationwide Series debut at New Hampshire driving for Baker Curb Racing the same year.
In 2011, Swindell drove the No. 16 Ford for Roush Fenway Racing in the Nationwide race at Dover, substituting for the ill Trevor Bayne. He qualified fifth and ran competitively before being eliminated in a controversial incident with Alex Kennedy. In 2012 he earned his first ARCA victory at Chicagoland Speedway, leading every lap from the pole. He also posted a career-best ninth-place Nationwide Series finish at Texas Motor Speedway with Biagi-DenBeste Racing.
For 2013 Swindell signed with Biagi-DenBeste Racing to contest 15 Nationwide Series races and compete for Rookie of the Year honors. He also made a Sprint Cup Series debut for Swan Racing at New Hampshire Motor Speedway later that fall. In August 2014, driving for Venturini Motorsports, he won an ARCA race at the Springfield Mile.
On August 13, 2015, during a heat race at the 55th annual Knoxville Nationals, Swindell's sprint car flipped multiple times. He sustained fractures to the L-1 and T-7 vertebrae and was initially paralyzed from the waist down. In a subsequent interview with journalist Robin Miller, Swindell reported that he had regained some feeling and movement in his legs during recovery, though the injury effectively ended his racing career.
Kevin Swindell's record of four straight Chili Bowl Nationals titles remains the benchmark for indoor midget racing. Combining precocious talent inherited from his father's lineage with success across multiple open-wheel and stock car disciplines, he was among the most versatile short-track competitors of his era before the 2015 accident cut his career short. His racing family legacy continued through the sport, and he remained active as an entrepreneur with his Swindell Speedlab and Victory Fuel brands.