Kaylee Bryson is from Muskogee, Oklahoma. Kaylee made her first attempt in the USAC National Midget Championship with Dave Mac Motorsports in 2019.
In 2021, Kaylee became the first female driver to qualify on pole at the Turkey Night Grand Prix, leading the first 17 laps and finishing fifth, the highest-ever finish for a woman in the event's history. Kaylee finished seventh in USAC National Midget points and was named the series' Most Improved Driver.