WATCH: Bryson DeChambeau nearly aces his latest golf challenge

Bryson DeChambeau is once again testing his skills off the course with a viral trick-shot challenge, and this time the task is as unusual as it is difficult. The two-time major winner, known for mixing golf with creative social media content, is attempting to chip a ping pong ball from the ground floor of his home into a shot glass placed upstairs. The challenge is known as the #ShotCupChallenge.

The challenge, sponsored by Underdog, comes with special rewards for fans. Each time he lands the ball inside a small yellow square around the glass, a fan will stand a chance to earn $100 of credit on the Underdog app, while a Bentley worth $325,000 is also up for grabs for a lucky fan if he finally makes the shot.

On Day 5, Bryson DeChambeau took 50 attempts at the target. After a few early misses, he found his rhythm and managed to land the ball in the yellow square. However, the ultimate goal of dropping the ball into the glass still remains unachieved.

Sharing the video on Instagram, DeChambeau captioned it as:

“What a way to end it 🥲”

This isn’t the first time the American is going viral with a unique challenge. He previously gained attention after hitting a hole-in-one over his house and onto his backyard green. That challenge took him 16 days to complete.

Keegan Bradley praised Bryson DeChambeau’s dedication after automatic qualification

Bryson DeChambeau didn’t need a captain’s pick to make it to Team USA. The 31-year-old earned his spot through strong performances, particularly at the majors, despite LIV Golf events not contributing ranking points. His consistency was enough to place him among the six automatic qualifiers.

Before announcing his captain’s selections, Keegan Bradley shared his thoughts on the players who had already secured their spots. Speaking about DeChambeau, the U.S. captain highlighted not only his results but also his commitment to the team.

“A lot to say about Bryson. One of the most incredible things was that he qualified for the team off of eight starts which is unheard of but what I am most impressed about Bryson is the effort that he has made to be a part of this team. He has had to travel, go out of his way to meet us in our places, and he has gone above and beyond what we would ever ask of a player and that’s the thing I am most proud of,” Bradley said [via Golfing Gazette].

He added, “You can go on and on about how good a player he is but what he has done for this team, and put in the extra effort, is amazing to see."

Bryson DeChambeau is now making his third Ryder Cup appearance after competing in 2018 and 2021. His record so far stands at 2-3-1. For the 2025 season, he ranked sixth in U.S. Ryder Cup points, 18th in the OWGR, sixth in Data Golf rankings, and second in true strokes gained (+1.70). He also clinched victory at LIV Golf Korea this year.