The entire Cincinnati Open Round of 16 is scheduled to be played Wednesday in both the men's and women's draw. An American underdog will look to add to his favorable head-to-head history against the top seed on the men's side, while another American that's enjoying the best stretch of his career tries to keep the good times rolling.
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All men's and women's singles matches at the Cincinnati Open 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.
Cincinnati Open Tennis Picks: Upset Alert
Tommy Paul (+203) vs. Alexander Zverev
Paul leads the head-to-head against Zverev, 2-1, with all three of their previous meetings having come on hard courts. The 24th-ranked American's willingness to get forward is frequently rewarded in fast court conditions like the ones here, and Paul's athleticism also helps him on the defensive end, where making Zverev hit extra balls can coax some subpar forehands from the top-seeded German. Zverev has been most vulnerable on hard courts in 2026, as he's 17-6 on hard courts and 29-6 on other surfaces this year.
Sorana Cirstea (+233) vs. Jessica Pegula
Cirstea has been a tough out all season in her final year on the WTA Tour, compiling a 36-12 record. The 36-year-old Romanian lost to Pegula on clay earlier this year, giving the third-ranked American a 2-1 edge in their head-to-head, but Cirstea has held her own against high-level competition with six top-20 wins in 2026, including a triumph over world No. 1 Aryna Sabalenka. Given Cirstea's level this year, she shouldn't be such a substantial underdog against any opponent.
Honorable Mention
Thiago Agustin Tirante (+184) vs. Jakub Mensik
Cincinnati Open Tennis Odds: Lock It In
Arthur Fils (-182) vs. Alex de Minaur
Fils is ranked No. 21, but he would likely be a top-10 player by now if not for injuries taking out chunks of his last two seasons. The 22-year-old Frenchman has been excellent when available this year, posting a 28-10 overall record and an 18-7 mark on hard courts. Fils has a significant edge in firepower over de Minaur, and the eighth-ranked Australian's court coverage is unlikely to hold Fils' onslaught at bay in these fast conditions. De Minaur is just 7-6 in his career at the Cincinnati Open and was pushed to a third-set tiebreak in his first match here by Fils' compatriot Quentin Halys, while Fils is coming off a top-15 win over Jiri Lehecka in the third round.
Lorenzo Musetti (-242) vs. Jaime Faria
Hard courts have historically been Musetti's least effective surface, but the 15th-ranked Italian has played his best tennis on hard this year, with a 12-5 record on this surface. He has steamrolled his way into the Round of 16 here, dropping only 10 games combined to Daniel Altmaier and Michael Zheng. The 79th-ranked qualifier Faria came into this tournament with a 2-6 career record in ATP Tour-level hard-court matches, and this is the first time the 23-year-old from Portugal has advanced to the Round of 16 at a Masters 1000 event.
Honorable Mention
Madison Keys (-425) vs. Xiyu Wang
Cincinnati Open Tennis Predictions: Value Bets
Brandon Nakashima (-156) vs. Nuno Borges
Nakashima is playing the best tennis of his career during this summer hard-court swing, with a 10-2 record since the conclusion of Wimbledon. The 22nd-ranked American's third-round win over No. 4 seed Daniil Medvedev was Nakashima's fourth top-20 win during this excellent stretch, as he defeated Jakub Mensik and de Minaur en route to the semifinals in Washington and Rafael Jodar during a Masters 1000 semifinal run at the Canadian Open. Nakashima is unlikely to slow down against the 47th-ranked Borges, who is having a nice tournament with top-25 wins over Francisco Cerundolo and Andrey Rublev but has a sub-.500 career hard-court record. The 29-year-old Borges has never reached the quarterfinals of a Masters 1000 event.
Honorable Mention
Linda Noskova (-126) vs. Amanda Anisimova
