Dollar signed with DGR-Crosley in October 2018 to drive part-time in what was then known as the NASCAR K&N Pro Series East as well as in the CARS Late Model Stock Tour. Dollar was put in the No. 54 car when the season started, and drove it for the first seven races of the year. He also drove the No. 17 in one race, the season finale at Dover. In his first race in the series and with his team, which came at New Smyrna, he qualified second, led 48 laps and finished ninth in the race. He ended up running almost all the races in his rookie season, only missing out on Watkins Glen, Bristol, Gateway, and New Hampshire. With his solid finishes, he was able to finish ninth in points. Also, Dollar competed in two ARCA Menards Series races for DGR-Crosley, driving their No. 4 Toyota at both Gateway and Kansas, finishing 6th and 7th, respectfully, as well as one K&N Pro Series West race at Phoenix in preparation for the new ARCA race at the track which was added to the schedule for the following year. In his first West Series start, he finished 18th after a crash. It was announced on December 19, 2019, that Dollar would be moving from DGR to Venturini Motorsports for the 2020 season, running full-time in ARCA in the No. 15 Toyota, replacing Christian Eckes, who moved up to the Truck Series full-time with Kyle Busch Motorsports after winning the 2019 series championship. Crew chief Shannon Rursch, who worked with Michael Self's No. 25 Venturini ARCA team in 2019, was announced to lead Dollar's No. 15 team in 2020. On June 20, 2020, Dollar got his first ARCA Menards Series win at Talladega. It was only his 5th start in the series.
Personal life
Drew has a younger sister named Allie, age 17. His parents names are Kim and Jimmy Dollar. According to his website, Dollar attended Marist High School and earned a 3.8 GPA. He was accepted into Texas Christian University, but decided not to immediately attend and defer his enrollment in order to focus solely on racing. He only started racing at age 15 when his parents agreed to let him drive a legends car if he got an A as his final grade in math in school that year. He played on the school's varsity tennis team on top of traveling back and forth from home to racetracks. While in high school, he also volunteered in homeless shelters and assisted living centers in Atlanta as well as being a eucharistic minister and confirmation leader at his church.
