2025 Cincinnati Open: Upsets, Favorites and Value Bets for Round 3 Monday
The third round of the Cincinnati Open begins Monday. This slate will include the first matchups of the tournament in which seeded opponents face each other. A pair of recent Canadian Open semifinalists are poised to keep rolling at the next WTA 1000 event, while a struggling seed on the men's side could be headed for yet another upset loss.
All Tennis Odds & Lines below are taken from DraftKings Sportsbook, but you can sometimes find more favorable odds for tennis betting by checking other best sports betting sites and sports betting apps. We offer exclusive sportsbook promos in states where sports betting has gone live.
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
Benjamin Bonzi (+225) vs. Stefanos Tsitsipas
Tsitsipas has been plummeting down the rankings and piling up losses, as he's just 5-7 in his last 12 matches and last notched back-to-back wins at Barcelona in April. He got a nice second-round win over 51st-ranked Fabian Marozsan following a first-round bye, but Tsitsipas still seems liable to lose to anyone given his recent results. Bonzi has had a subpar season, but he's coming off a top-10 win over Lorenzo Musetti in the second round and also notched another such victory at Wimbledon over Daniil Medvedev, so the Frenchman won't be intimidated against the formerly third-ranked Tsitsipas, who has dropped all the way down to 29th.
Ashlyn Krueger (+160) vs. Jasmine Paolini
Paolini's just 4-5 in her last nine matches, with three of those defeats coming against opponents ranked outside the top 60. While she retained some of last year's magic on clay, Paolini hasn't been nearly as effective since the action switched back to faster surfaces. Krueger will have the crowd in her corner, and the 35th-ranked American has a golden opportunity to pick up one of the biggest wins of her young career. The 21-year-old Krueger's best results have come on hard courts, where she has already notched five top-20 wins in 2025.
Honorable Mention
Dayana Yastremska (+290) vs. Coco Gauff
Cincinnati Open Tennis Odds: Lock It In
Elena Rybakina (-250) vs. Elise Mertens
The ninth-seeded Rybakina has been on a nice roll during the American hard-court swing, with a 7-2 record that includes a semifinal showing at the Canadian Open. The 19th-seeded Mertens is a high-floor, low-ceiling player who usually falters against superior opponent such as Rybakina, who has a significant edge in power on her serve and groundstrokes. Rybakina leads their head-to-head 5-1, and the last four encounters have been straight-sets Rybakina wins.
Amanda Anisimova (-225) vs. Anna Kalinskaya
Anisimova has played elite tennis since the start of the French Open, with an 18-5 record and only one loss to an opponent outside the top 20 over that span. The big-hitting American will look to keep rolling against the 34th-ranked Kalinskaya, who is just 17-15 in 2025. Anisimova won their only previous matchup at last year's Canadian Open.
Honorable Mention
Tommy Paul (-400) vs. Adrian Mannarino
Cincinnati Open Tennis Predictions: Value Bets
Jessica Bouzas Maneiro (+105) vs. Taylor Townsend
Bouzas Maneiro has had an impressive last few months, starting with the 6-0, 6-1 drubbing she put on Emma Navarro en route to reaching the third round at the French Open. Since then, the 42nd-ranked Spaniard reached the Round of 16 at Wimbledon and quarterfinals at the Canadian Open. She already has a nice win over No. 21 seed Leylah Fernandez in this tournament, and Bouzas Maneiro is well positioned to keep rolling against the doubles specialist Townsend, who is ranked No. 1 in doubles but 126th in singles.
Clara Tauson (-165) vs. Veronika Kudermetova
There should be no shortage of big hitting in this one, but Tauson's likely to execute that game plan better based on her recent form. The surging Dane is coming off an impressive semifinal run at the Canadian Open, which included straight-sets wins over 2025 Grand Slam champions Iga Swiatek and Madison Keys. The 22-year-old Tauson currently boasts the best ranking of her career at No. 15, while the 28-year-old Kudermetova peaked at No. 9 in 2022 but has been floating around the unseeded range the past two years and is currently ranked 36th.
Honorable Mention
Frances Tiafoe (-165) vs. Ugo Humbert
