By Cole Cusumano

Last year, 2019 breakout driver Matt DiBenedetto stole the hearts of the racing world with his unrelenting determination and underdog success. Prior to the start of the 2020 NASCAR Cup Series season, he set forth a pair of goals for his debut in piloting the famed Wood Brothers Racing No. 21 — contend for wins and make the playoffs.

In tallying as many top-10s as last season, including matching a career-best runner-up finish, as well as besting seven-time Champion Jimmie Johnson for the final postseason spot, the Cinderella saga continues.

With 10 races remaining in 2020 and a shot at the title, what’s next on his checklist?

“I absolutely would love to get that 100th win for the Wood Brothers,” DiBenedetto told POPULAR SPEED. “That would be an amazing goal to accomplish. I’d say now that we’re in the playoffs, just focusing on executing and making the most of what we have.”

As has been the case with his career, DiBenedetto realizes he’s entering the playoffs as the 16th seed and a definitive underdog. Acknowledging he’ll have to outpace the likes of competitors such as Aric Almirola, Clint Bowyer and brothers, Kyle and Kurt Busch in the Round of 16, he’s focusing solely on himself and taking it one race at a time.

“We’re competing for a championship,” DiBenedetto said. “This is the time to shine, for sure, and hopefully we can make it down to the end. This is a great opportunity for us to capitalize on now that we’re all closed in points-wise and within striking distance. We’re the most prepared as a team to go out there and pick off a lot of guys.”

The task at hand begins with the highly coveted Southern 500 from Darlington Raceway. With two top-10s including one in May, DiBenedetto has been successful as of late in taming ‘The Lady in Black,’ but there’s a reason it’s notoriously considered the toughest track on the circuit.

“Darligton’s a little unique in the sense that it’s a place where you need to focus on racing the track, not quite as much racing other people,”DiBenedetto revealed. “You focus on minimizing your mistakes, racing the track, making good adjustments. You’re kind of focused on yourself and your team, and not smacking the wall — things like that, that could end your day.”

Although the 1.366-mile venue presents many obstacles, the No. 21 paying tribute to Tiny Lund will roll off an admirable 11th in the crowned-jewel event. Expanding further upon the opening round of the playoffs, Bristol Motor Speedway will serve as the cutoff race. The primetime spectacle last season served as DiBenedetto’s career-defining moment thus far, leading a race-high 93 laps and finishing runner-up.

Given his impressive history at Darlington and Bristol, this challenging round for most drivers should play to DiBenedetto’s strength. Richmond International Raceway may prove to be difficult, as he hasn’t finished above 14th there, but this trio of tracks overall should help the driver of the No. 21’s case to potentially cross off both boxes for his new pair of goals.