2021 marks the seventh year of competition in the NASCAR Cup Series for Matt DiBenedetto and his second year with the longest-running Cup Series team, Wood Brothers Racing and the iconic No. 21 Ford Mustang. Beginning in 2015, Wood Brothers Racing formed a technical alliance with Team Penske and they will continue that partnership with DiBenedetto at the helm of the No. 21 while they compete for their 100th Cup Series win.
By the age of 13, DiBenedetto had moved to North Carolina and in the years following he competed on several occasions racing late models, when he was noticed by Joe Gibbs Racing (JGR) in 2008. In 2009, JGR gave DiBenedetto the opportunity to run in their NASCAR K&N Pro Series East car in seven events for the organization. DiBenedetto won two events that year at Tri-Country Speedway and Loudon, along with three poles in his first year. JGR also put DiBenedetto in one of their NASCAR Xfinity Series (NXS) cars that year at Memphis International Raceway. 2010 through 2014 saw the Grass Valley, CA native make 50 starts in both NXS and the ARCA Menards Series.
2015 marked the first year DiBenedetto would get his shot at the NASCAR Cup Series. He was initially meant to split the seat time of the No. 83 of BK Racing with Johnny Sauter, but after Sauter ran the Daytona 500 and decided to focus on the NASCAR Gander Outdoor Truck Series, DiBenedetto was named the full-time driver. DiBenedetto returned to BK Racing in 2016 and scored his first career top-10 finish in the Cup Series at Bristol Motor Speedway.
In 2017, DiBenedetto competed for Go Fas Racing in the No. 32. He captured another top-10 finish when he crossed the yard of bricks in eighth place at the famous Indianapolis Motor Speedway. Soon after that finish, it was announced that DiBenedetto would return to the No. 32 for the 2018 season. Late 2018 brought more change in the career of the young driver when the announcement came that DiBenedetto would be transitioning to the No. 95 car in 2019 for Leavine Family Racing. DiBenedetto captured three top five and seven top-10 finishes. His best finish came at Bristol Motor Speedway where he led 93 laps under the lights. Late-race damage would cause him to lose the lead with 11 laps remaining and go on to finish second.
Two days before his incredible run at Bristol, DiBenedetto received the news that he would not be returning to the driver seat of the No. 95 car for 2020. A little less than a month later, on September 10th of 2019, Wood Brothers Racing announced that DiBenedetto would pilot their famed No. 21 car for the 2020 season. DiBenedetto had his most successful year to date in 2020, finishing 13th in the NASCAR Cup Points Standings with three top five and 11 top-10 finishes.