Sports News
| Published On Aug 29, 2025 2:40 am CEST  |  Updated on Sep 11, 2025 7:07 am CEST | By iGaming Team

Bryson DeChambeau Teams With Underdog for Bentley Giveaway

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Bryson DeChambeau is at it again. The 31-year-old golfer, fresh off preparing for the Ryder Cup, has been filling his social channels with daily trick-shot attempts that now carry some pretty high stakes: one lucky fan could end up driving away in a Bentley Continental valued at $325,000.


Good to know

  • DeChambeau has been attempting to land a ping pong ball into a tiny plastic cup each day.
  • Every failed day adds 10 more tries to the next attempt.
  • The eventual winner will be revealed on Instagram Live the day after he makes the shot.

Since Monday, DeChambeau has been trying to sink a ping pong ball into a shot glass, ramping up the drama with each miss. His most recent attempt saw him take 40 swings at it, but while he missed again, he did give three fans a $100 Underdog credit.

The contest is tied to DeChambeau’s partnership with Underdog Fantasy, where new players can also claim sign-up perks tied to daily fantasy contests and pick’em games. Once the ball finally lands in the cup, an Instagram Live will follow the next day, naming the fan who will drive away in the luxury car.

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DeChambeau the Influencer

DeChambeau isn’t just known for his power on the course. Off it, he’s built a massive online following, with his YouTube channel closing in on 2.4 million subscribers. His “Break 50” series has featured appearances from Adam Sandler for Happy Gilmore 2 and even former President Donald Trump.

For Bentley Motors, the partnership is nothing new—DeChambeau has long been a brand ambassador, often arriving at tournaments behind the wheel of one of their cars.

Always Entertaining

Love him or not (at iGaming.org we sure love the guy), DeChambeau brings a unique energy to golf. His past trick-shot ventures include a marathon effort last fall when he tried for weeks to land a hole-in-one over his mansion roof. After two weeks, on day 16 to be exact, of wedge practice, he finally pulled it off as you can see in the below video:

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UPDATE 11/9: Mission Accomplished!

On the twelfth day of trying, Bryson was finally able to get the job done. While having reserved 120 balls for him to try on the day, he didn’t need all of them. Counting up the totals for all of the 11 previous days, it took him over 660 attempts. You can see the winning moment here below: