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Matt DiBenedetto searching for historic win, redemption at Road America

It has been nearly two years since Matt DiBenedetto was last seated in a race car at Road America, the site of this weekend’s NASCAR Cup Series Jockey Made in America 250 presented by Kwik Trip (2:30 p.m. ET, NBC/NBC Sports App, MRN, SiriusXM NASCAR Radio). A lot of things have changed since then, but for DiBenedetto, the focus remains on a race for redemption and a chance to solidify his name among renowned names in NASCAR history.

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DiBenedetto’s lone start at the technical, 14-turn Wisconsin track came in 2019 by way of an Xfinity Series seat for Joe Gibbs Racing. In a field packed with skilled road-course drivers like AJ Allmendinger, Christopher Bell, Chase Briscoe and Austin Cindricc, it was DiBenedetto who led almost twice as many laps as anyone else in the 38-driver field. Chasing down race-leader Bell on the final lap, DiBenedetto spun in the final turn and limped home with a 27th-place finish.

“We led a lot of laps but we kinda threw the race away,” DiBenedetto told NASCAR.com. “I wish we could go back and redo that one. We were easily the fastest car on the race track and I made mistakes, we had a blow-up of a pit stop and I didn’t do a good enough job of trying to recover from that many mistakes and yeah, the win slipped away from us. That one still haunts me to this day.”

Now, the driver in his second season with the Wood Brothers Racing is focused on controlling the positives and capitalizing on a new opportunity this weekend.

“It’s still encouraging though that we were really fast,” DiBenedetto said. “[Road America] is a track that I really love and it’s one of my favorite places that we go to. So there are a lot of positives on that side of it and I’m fortunate that I have been there a few times.”

With NASCAR’s premier series heading back to Elkhart Lake for the first time since 1956, DiBenedetto’s in-race experience gives him a slight edge with the No. 21 crew pushing for consecutive playoff berths for the first time under the new format. Entering the weekend, DiBenedetto’s camp sits 60 points behind 14th place in the playoff standings, the current cutline (based on drivers that don’t have wins in the standings).

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“Our number one goal has been to make the playoffs,” DiBenedetto said. “I’ll be honest, we’ve had probably the roughest luck, circumstances, whatever you want to call it in my career this year. It just feels like nothing is lined up, we have not had smooth races and when we do, it’s like, ‘Alright, yeah we have a top 10 run going’ and then we have an electrical issue or something. It’s just been one thing after another.”

Through race 19 out of 36, DiBenedetto remains winless and is on pace for fewer top 10 runs than a season ago when he had a career-best 11 top-10 finishes. In early June, the team made a major change, tasking Jonathan Hassler — a long-time Team Penske engineer — with getting them back on track for a late-season push.

But the changes and adversity haven’t distracted him from one of his biggest personal goals — a historic milestone that would turn the entire season, and perhaps his career, around.

“I really want to get that 100th win for the Wood brothers,” DiBenedetto said. “We have the strength to do that as a team, just need some things to fall a little bit our way.”

Sitting on 99 wins since Ryan Blaney’s 2017 triumph at Pocono Raceway, the milestone victory for DiBenedetto would solidify him among all-time great names for the longest continuously operating team in the series. It would also mark his first career victory in the Cup Series. He nearly achieved the goal a season ago, finishing a heartbreaking runner-up in both races at Las Vegas Motor Speedway. He also led taking the white-flag lap at Talladega Superspeedway this spring.

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In spite of all the pressure as the regular season winds down, DiBenedetto is confident that he and his team are moving in the right direction.

“Like many teams, we have had to work improving our road course program,” DiBenedetto said. “We were a little weak there. But I think we are making some gains and I’m excited to see where we fall at Road America.”