Born in Level Green, Pennsylvania, Benning began racing as a fifteen-year-old at Heidelberg Raceway, despite the minimum age requirement being eighteen. He has also raced in dirt late models and asphalt modifieds.
In ARCA, Benning finished in the top ten in points seven times, with a highest place of fifth in 2001. In 276 ARCA starts, he recorded five top-fives and 32 top-ten finishes, with a best result of third place at the Springfield dirt mile in 2004.
Benning made his NASCAR debut in 1989, driving in three Cup Series races for the No. 99 car owned by Jerry O'Neil. He started 35th and finished 30th in his debut at Dover, matching that finish at Pocono and recording 31st in his return to Dover.
Benning made his last Cup points race start for O'Neil in 1993, starting last (39th) at Darlington and finishing 39th after one lap. After that, he attempted to make the Daytona 500 for seven consecutive years but either failed to qualify or was denied entry due to his car being slow in practice. He attempted many Cup races through 2001 in his own No. 84 84 Lumber Chevy, as well as a couple of entries in the No. 79 T.R.I.X. Racing car. Benning attempted a total of 33 Cup races but did not qualify 29 times; he withdrew from the 2011 Daytona 500.
In the NASCAR Busch Series, Benning was able to compete in three of the six races attempted. In his debut, Benning started the 2003 Nazareth race in 42nd and finished 40th. He later improved with a career-best 36th place at NHIS. Driving again at Nazareth, brake failure forced him out of the race in 38th. He fielded a car for Dion Ciccarelli at Nazareth in 2004, with a 29th-place result.
Benning's next NASCAR start came in the Craftsman Truck Series in 2002, driving for Troxell Racing. He qualified the No. 93 Chevy into the field at Nashville Superspeedway in eighteenth position, but a vibration dropped the team out and Benning finished 32nd.
During the 2008 season, Benning competed in seven of the eight races attempted, driving his own No. 57 Chevrolet. In 2009, he competed full-time in the Truck Series β his first attempt at a full NASCAR season β qualifying for 24 of 25 races and finishing 21st in overall points. His best finish came at Michigan when he finished seventeenth with Germane Red sponsorship.
In 2013, Benning held onto fifth place after a hard-fought battle with Clay Greenfield in the "Last Chance" qualifying race at Eldora Speedway to earn the final transfer spot into the inaugural Mudsummer Classic. His truck sustained significant damage, but he was able to make repairs with the help of members of larger teams and went on to finish 26th, four laps down. Benning's performance in the last chance race was popular with fans; afterward, he placed the Eldora truck for sale on eBay.
Later that season, Benning obtained his career-best Truck Series finish of twelfth at Talladega Superspeedway.
During 2014, Benning changed from his iconic No. 57 to the number 6, with the 57 becoming the part-time second entry. Late in the season, Benning gained backing from Pennsylvania governor Tom Corbett.
In 2015, Benning finished fourteenth in the opening race at Daytona and was tenth in points. He scored his best career start of thirteenth during the 2015 Mudsummer Classic and finished nineteenth after rebounding from a late-race spin. The end of 2015 was a struggle, with Benning missing four races late in the season.
2016 began with DNQs at Daytona and Atlanta. Benning failed to qualify for six races and withdrew from Charlotte. He missed the race in Texas by .016 seconds after being knocked out by Austin Hill. After missing races, Benning partnered with MB Motorsports at Kentucky, starting 30th and finishing 28th. He managed to qualify for only eight races while failing to qualify for eight others and withdrawing from five.
In 2017, Benning missed the first three races of the season. He made the 4th race at Kansas after only 32 trucks showed up for the 32-truck field, then made every race he attempted for the rest of the season.
In 2018, Benning made every race until the regular-season finale at Bristol. After Canada, he failed to make Las Vegas through Martinsville and did not appear for the rest of the season.
In 2019, during drafting practice at Daytona, Benning's No. 6 Silverado sat 6th fastest, but the team lacked single-truck speed and ultimately missed the field. Results across the season were mixed, though the second Texas race resulted in a seventeenth-place finish, followed by 24th and 25th at Iowa and Gateway. An 18th-place finish at Talladega was followed by an accident at Martinsville that ended his season early.
In 2020, Benning again missed the cut at Daytona. Following the two-month racing hiatus, Benning looked to take advantage of NASCAR's field expansion from 32 trucks to forty, but found himself excluded from races at Charlotte and Atlanta when 47 trucks entered each time. At Homestead, with only 39 teams entered, Benning made his first start of the season. He posted a best finish of 22nd at Talladega Superspeedway and a points finish of 36th.
Benning announced plans to attempt the full 2021 NASCAR Camping World Truck Series schedule, starting a fundraising campaign called "Racing With The Ultimate Underdog." He picked up sponsorship from MDF A Sign Company heading into Daytona and, after several years of running a plain paint scheme, added red and yellow accent to his truck. He narrowly missed qualifying for the season opener but made the second race at the Daytona Road Course thanks to NASCAR's suspension of qualifying for much of the 2021 season.
Benning took advantage of Camping World CEO Marcus Lemonis' offer of $15,000 to any team running in Las Vegas and Atlanta with Camping World and Overton's paint schemes. He scored a top-twenty at Knoxville despite being involved in a late accident. At Gateway, officials notified him that his truck's nose was no longer legal, forcing a withdrawal. He later returned with a new nose at the second Darlington race and scored a seventeenth-place finish at Talladega with sponsorship from Cross-Eyed Owl Brewing. For the season finale, Benning obtained a Niece Motorsports prepared truck along with an Ilmor engine, but problems before qualifying resulted in a DNQ.
Prior to 2022, NASCAR introduced an updated body style for the Truck Series starting at Daytona; the 2019β2021 bodies remained legal at other tracks. Unable to afford the new body, Benning skipped the Daytona opener β the first time he had done so since 2008 β and did not appear until the second annual Bristol Dirt Race, where he fell short in his heat race. He missed Knoxville, then failed to qualify at Pocono when rain washed out qualifying. He made one last attempt at Richmond but again fell short.
On February 14, 2023, it was revealed that Benning would attempt to qualify for the Daytona race driving the No. 46 Toyota for G2G Racing, replacing Johnny Sauter.
At the 2023 Weatherguard Truck Race on Dirt at Bristol Motor Speedway, after rain washed out Friday practice, Benning ran near the tail of the field for the first nine laps of his qualifier. On lap ten, he took advantage of issues for Tyler Carpenter and Andrew Gordon, finishing 8th and earning the last transfer spot into the main event. Starting 30th, Benning completed the race in 24th position, becoming the oldest driver in NASCAR history to finish on the lead lap at 71 years of age. This was also his first race with new crew chief Dan Killius and spotter Rob Tate Jr.
At the Tyson 250 at North Wilkesboro Speedway, after only two laps of practice, Benning lost control heading into turn 3 and backed into the wall. TV coverage by Fox Sports showed the all-volunteer crew of Norm Benning Racing immediately set to work to repair the truck. It was repaired in time for Saturday morning technical inspection, but Benning fell short of qualifying. He later entered the Toyota 200 at World Wide Technologies Raceway, qualifying 30th and finishing 28th.
In 2024, Benning failed to qualify at Milwaukee. At Talladega in the Love's RV Stop 225, he qualified 31st of 38 teams and finished 21st β his highest finish since the same race in 2021 β after running in the lead pack for the first stage before being spun on pit road and subsequently getting the lap back. At Martinsville's Zip Buy Now, Pay Later 200, Benning locked into the race when Josh Reaume withdrew his No. 27 entry, shrinking the field to 36 trucks. He did not make a lap in practice and qualified 34th, ultimately falling out after seventeen laps with brake failure and finishing 36th.
In 2025, Benning announced a part-time schedule including Daytona, both Martinsville races, and Talladega. After practice was rained out at Daytona, he qualified 22nd and finished sixteenth, becoming the oldest driver to finish on the lead lap at 73. His next two attempts at Martinsville and Bristol both resulted in DNFs and 34th-place finishes.
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