This article is part of our Tennis Picks series.
Much of the United States will enjoy a day off Monday for Labor Day, but it will be business as usual at the USTA Billie Jean King National Tennis Center in New York City, where U.S. Open fourth-round play is scheduled to wrap up. Top women's seeds will look to hold off upset bids by surging challengers, while favorites on the men's side are in good position to keep rolling.
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All men's singles matches at Grand Slams such as the U.S. Open are best of five sets, while women's singles matches are best of three sets. A mix of players' previous hard court results, recent form and stylistic matchups can help pinpoint intriguing betting opportunities, both among favorites likely to cruise to victory and underdogs ready to pull off upsets. The aforementioned underdogs are highlighted in the Upset Alert section, the Lock It In section covers players who can safely be viewed as overwhelming favorites, while the Value Bets section recommends enticing options in matchups that are considered closer to toss-ups.
U.S. Open Picks: Upset Alert
Tomas Machac (+210) vs. Jack Draper
It wouldn't be surprising if all four favored men won Monday, but Machac has the best chance of spoiling the party. The 23-year-old Czech is ranked 14 spots behind Draper at No. 39, but Machac won their only previous meeting earlier this year on clay, and he also defeated Draper in a pair of non-ATP Tour matches while they were working their way up the Future/Challenger circuits. Machac has a win over Novak Djokovic this year and claimed the mixed doubles gold medal at the Olympics, so he's unlikely to be intimidated by the big stage in his first Grand Slam fourth round. Draper lost at this stage in last year's U.S. Open, and while the big-serving lefty has a strong hard-court game, his 15-8 record and on the surface this year isn't meaningfully better than Machac's 13-8 mark.
Diana Shnaider (+180) vs. Jessica Pegula
These were two of the hottest players on the WTA Tour heading into the U.S. Open, and they have showed no signs of cooling down, with neither dropping a set through three rounds. In August, Pegula won the Canadian Open and reached the final of Cincinnati. She beat Shnaider 6-4, 6-3 in the Canadian Open semifinals, marking a rare loss for the 20-year-old lefty in an ongoing 22-5 stretch during which Shnaider has captured two titles. Pegula's attempt to troll Jets fans in a post-match interview didn't exactly ingratiate the daughter of the Bills owners to the New York City crowd, but she should still have majority support in this match, though Shnaider's no stranger to playing in hostile environments after a one-year college tennis stint at NC State. Like her parents' team, Pegula has never won when it matters most, as she's 0-6 in Grand Slam quarterfinals and hasn't even been to that stage since Wimbledon last year despite consistently being ranked in the top six. Given Pegula's history of underperforming in the second week of majors, Shnaider has a great chance to turn the tables in this rematch.
Honorable Mention
Liudmila Samsonova (+600) vs. Iga Swiatek
U.S. Open Odds: Lock It In
Jannik Sinner (-600) vs. Tommy Paul
With Carlos Alcaraz and Novak Djokovic out of the picture, this is Sinner's tournament to lose on the men's side, and he has certainly looked the part of the favorite by raising his level with each match. Paul has the tools to hang in extended rallies with Sinner despite the Italian's edge in power, but the biggest difference between these two comes in how well they take care of their own serve. Sinner didn't face a break point in his third-round match and has broken 21 times while losing serve six times in this tournament while Paul allowed 143rd-ranked Gabriel Diallo to break him five times in the third round. Sinner leads their head-to-head 2-1, including a straight-sets win last year in their only hard-court meeting.
Alex de Minaur (-350) vs. Jordan Thompson
De Minaur has looked more and more confident in the health of the hip he hurt at Wimbledon, and the Australian has played at a top-10 level throughout 2024, so he has deservedly returned to a top-10 spot in the live rankings heading into this match with 32nd-ranked Aussie compatriot Thompson. De Minaur has won four of their previous five matches, including straight sets victories in all three of their hard-court meetings. The speed demon's counterpunching game matches up well against Thompson, who lacks the power to blast the ball past de Minaur consistently and will be forced into hitting a lot of extra balls to end rallies.
Honorable Mention
Daniil Medvedev (-650) vs. Nuno Borges
U.S. Open Predictions: Value Bets
Jasmine Paolini (+125) vs. Karolina Muchova
This matchup between two of the most well-rounded players on the WTA Tour could go either way, but Paolini should be a slight favorite rather than a slight underdog. The fifth-ranked Italian is three wins away from playing in a third consecutive Grand Slam final, while Muchova has just 10 wins all year after missing most of 2024 due to a wrist injury. Muchova seems to be approaching the level that helped her reach the semifinals here last year, but there's no substitute for experience in tight matches, which is something Paolini has accrued plenty of this year and Muchova has lacked. The contrast between Muchova's touch and Paolini's relentless offense off the ground should be fascinating to watch, but in a match that will likely come down to a few key moments late in sets, Paolini is better equipped to excel in the most important points as she has been doing all year.
Honorable Mention
Beatriz Haddad Maia (-110) vs. Caroline Wozniacki
