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2026 US Open First Round Best Bets for Monday 8/31/26

2026 US Open First Round Best Bets for Monday 8/31/26

Published:

By: Blake Krass

The US Open first round continues on Monday. It was a great first day of action on Sunday, and there are only more exciting matchups on this Monday slate.

Here are my best bets for Monday of the first round of the 2026 US Open.

2026 US Open First Round Best Bets

Arthur Fils to win 3:0 vs. Stefanos Tsitsipas (+150)

Arthur Fils has a chance to go on a real run at this US Open. Fils is one of the most promising young players in the sport, but has struggled with injuries over the past two years. He missed last year’s US Open, as well as the first two majors of this year. However, Fils has played excellent tennis at the other big events in 2026. He has played in six ATP Masters 1000 events this year and made at least the quarterfinals in five of them. Fils just won his first career Masters 1000 title in Cincinnati ahead of this tournament. He is in the best form of his life, and at the perfect time to make a run at his first major title.

Stefanos Tsitsipas does not have the game he once had to challenge a player like Fils in peak form. Between majors and Masters 1000 events, Tsitsipas has played in 10 high-profile tournaments this year. He has only made it past the second round in two of those 10 events, and has never made it past the fourth round. In his young career, Arthur Fils is already 5-0 against Stefanos Tsitsipas. In their one meeting this year, Fils dismantled him 6-0, 6-1 in Miami. Fils should take care of Tsitsipas in straight sets here in New York.

Taylor Townsend to win 2:0 vs. Maja Chwalinska

Maja Chwalinska had a magical, once-in-a-lifetime run to the Roland-Garros final earlier this summer. She became one of just two players in the Open Era to make a major final as a qualifier. However, since that special run, it has been a hard crash back down to earth for Chwalinska. She was bounced in the first round at Wimbledon and the Canadian Open, then lost in the second round in Cincinnati. She tried to get one more run in before the US Open after her early exit in Cincinnati, only to get bounced in the first round in Monterrey.

Taylor Townsend should take care of Chwalinska in two sets. Townsend is primarily a doubles player, but she has had more recent success than Chwalinska in singles. Townsend picked up a nice win over Marie Bouzkova to make the Round of 32 in Canada, where she put up a great fight against Belinda Bencic. Townsend has had really tough draws at the majors this year, having to face Iga Swiatek and Coco Gauff in the first rounds at Wimbledon and Roland-Garros. This is a chance for her to pick up a nice win at a Grand Slam, and she should do so.

Last year, Townsend tied her career-best US Open singles finish by making it to the fourth round on the back of upsets over Jelena Ostapenko and Mirra Andreeva. Townsend will have the home crowd at her back and should use that to push to a straight-set victory against Maja Chwalinska.

Blake Krass has contributed to DraftKings since 2024, and is a content creator with a specialty in sports betting. Blake primarily focuses on college football and NFL coverage but will also be covering college basketball, the NBA, MLB and more. Prior to arriving at DK, Blake was a sports betting writer for The Action Network.
Disclaimer

I am a promoter at DraftKings and am also an avid fan and user and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.