Bryson DeChambeau Partners with Underdog for Trick Shot Challenge

The world’s 18th-ranked golfer and two-time U.S. Open Champion is posting daily videos promising to give away a Bentley if he sinks a nifty trick shot.

Jori Negin-Shecter - Contributor at Covers.com
Jori Negin-Shecter • News Editor
Aug 28, 2025 • 17:37 ET • 4 min read
Photo By - Imagn Images.

Bryson DeChambeau is back to his trick-shot ways, with a new partnership potentially set to turn one lucky fan into the brand-new owner of a Bentley Continental.

Key Takeaways

  • Bryson DeChambeau is looking to give away a brand new Bentley Continental thanks to his newest partnership with DFS platform Underdog.

  • DeChambeau will be tasked with hitting a ping pong ball into a plastic shot glass, with fans gaining bonus credits when he gets close and lands in the “Underdog Zone.”

  • The top-ranked golfer will give away the car on an Instagram Live to a random viewer the day after his successful shot.

Since Monday, the 31-year-old has been making daily uploads across his social media channels in which he attempts to sink a ping pong ball into a plastic shot glass. He’s gotten close but is yet to cash in for the lucky prize winner.

In his latest effort, despite taking 40 shots at the plastic shot cup - the number of shots goes up by 10 for each failed day - DeChambeau was ultimately unsuccessful, though he did line up a trio of fans with a $100 credit for Underdog.

New players can also take advantage of Underdog Fantasy’s sign-up bonus, which offers perks for users looking to get into daily fantasy contests and pick’em games.

Once the unlikely shot does fall into the cup, a next-day Instagram Live will take place, with the winner taking home the car valued at $325,000.

DeChambeau has become something of an influencer in recent years, with his YouTube channel approaching 2.4 million subscribers thanks to partnerships like his newest with Underdog, as well as collaborations in his "Break 50" series with the likes of Adam Sandler for "Happy Gilmore 2" and Donald Trump while the President was on the campaign trail.

An engaging personality

DeChambeau’s big personality has been a breath of fresh air for the world of golf to some, while to others he's more of a controversial character prone to rocking the boat. That doesn’t seem to bother the star linksman, whose latest foray into trick shots is nothing out of the ordinary for him.

The Modesto, Calif., native spent several days last fall trying to nail a hole-in-one over his mansion, eventually sinking it after a full two weeks of wedge work.

DeChambeau has also partnered with Bentley Motors as a brand ambassador for several years, often showing up to tournaments with the ride in tow.

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Jori Negin-Shecter - Covers
News Editor

Jori Negin-Shecter is a sports writer and podcast host, with previous work featured in publications including Sportsnet.ca, Yahoo Sports Canada, and the Nation Network. In addition to joining Covers in 2024 as a contributor, Jori also works as an Associate Producer on Sportsnet Central, and co-hosts the Bird's Eye View Podcast, a show focused on the Toronto Blue Jays.

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