at Martinsville, that would ultimately end his season early. 2020 would begin the same as 2019, with Benning missing the cut at Daytona. Benning chose not to make the trip to Las Vegas and had no clear plans for the season. Following the 2-month racing hiatus, Benning looked to take advantage of NASCAR's field expansion, from 32 trucks to 40. However, Benning found himself excluded from the races at Charlotte and Atlanta when 47 trucks entered each time. The following race at Homestead, only 39 teams entered, allowing Benning to make his first start of the season. He made all other attempted races skipping the other Las Vegas race and the finale at Phoenix Raceway. Benning posted a best finish of 22nd at Talladega Superspeedway, and a points finish of 36th. Benning would announce plans to attempt the full 2021 NASCAR Camping World Truck Series schedule. Shortly after, Benning would start a fundraising campaign called "Racing With The Ultimate Underdog". Benning would pick up sponsorship from MDF A Sign Company heading into Daytona, and, after several years of running a plain paint scheme, Benning would add red and yellow accent to his truck. Benning would just miss out on qualifying for the season-opening race, but by finishing in the top 40 in points in 2020, Benning would make the second race at the Daytona Road Course, thanks to NASCAR's no qualifying for the majority of the 2021 season. Benning would take advantage of Camping World CEO Marcus Lemonis' offer of $15,000 to any team who ran at Las Vegas and Atlanta with Camping World and Overton's paint schemes. After lackluster results most of the season, Benning was able to score a top 20 finish at Knoxville despite being involved in a late accident. At Gateway, Benning was notified by officials that his truck's nose was no longer legal, forcing him to withdraw. Benning would show at the second Darlington race with a new nose. Benning would score another top 20, a 17th, at Talladega, with new sponsorship from Cross-Eyed Owl Brewing. For the season finale race, Benning was able to get a Niece Motorsports prepared truck, along with an Ilmor engine. However, problems before qualifying plagued the 6 team, and Benning turned the slowest lap, resulting in a DNQ. Benning did say he and his team would be back in 2022. Prior to the start of the 2022 season, NASCAR