This article is part of our Tennis Picks series.

Thursday at the Cincinnati Open will be dedicated to second-round play after a few second-round matches were sprinkled in along with the conclusion of the first round Wednesday. One of the top seeds in the women’s draw could face a tough challenge from a player with recent experience in pulling off notable upsets, while a few players who have been making moves up the rankings recently will look to build on their recent success.

All Tennis Odds & Lines are taken from DraftKings Sportsbook, but you can sometimes find more favorable odds on some of these matches by checking mobile sportsbooks such as FanDuel Sportsbook, BetMGM, Caesars Sportsbook, or any of the other best sports betting sites. We offer exclusive sign-up bonuses for some of those sportsbooks 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

Yulia Putintseva (+265) vs. Coco Gauff

Gauff is the defending champion here, but Putintseva’s a tough second-round draw for the No. 2 seed, especially since Gauff will be adjusting to the conditions here after a first-round bye. Putintseva took a set to adjust in her first-round match but stormed back to beat Harriet Dart 4-6, 6-0, 6-1. The world No. 34 is coming off an excellent grass-court season that included a title in Birmingham and an upset over world No. 1 Iga Swiatek at Wimbledon. Putintseva also played well on hard courts earlier this season, posting a 7-2 record during the Sunshine Double of Indian Wells and Miami while reaching the quarterfinals of the latter WTA 1000 event. Gauff’s speed should help her counter Putintseva’s frequent drop shots, but while the American leads their head-to-head 3-0, all of those matches came on clay and two came down to 6-4 in the third set.

Jack Draper (+160) vs. Stefanos Tsitsipas

Tsitsipas lost to Kei Nishikori in his first match in Toronto last week, and he barely squeaked by Jan-Lennard Struff 4-6, 6-4, 6-3 here. The world No. 11 is just 12-7 on hard courts in 2024 compared to 22-6 on clay, so he has been vulnerable on this surface all year, and Draper has a lot more weapons on this surface than Nishikori or Struff at this stage of their respective careers. The big-serving British lefty has stepped up in big matches in his young career, as Draper defeated Carlos Alcaraz in June. Draper has had some issues controlling his temper lately, but there’s no doubt the 28th-ranked 22-year-old has the talent to beat Tsitsipas again after upsetting Tsitsipas at the 2022 Canadian Open in their only previous meeting.

Honorable Mention

Karen Khachanov (+265) vs. Alexander Zverev

Cincinnati Open Tennis Odds: Lock It In

Hubert Hurkacz (-275) vs. Yoshihito Nishioka

Hurkacz looked noticeably rusty last week in his first tournament since a knee injury knocked him out of Wimbledon, but he still managed to reach the quarterfinals of the Canadian Open before losing a 3-6, 7-6 (5), 7-5 heartbreaker to eventual champion Alexei Popyrin. The 6-foot-5 Pole has the ability to serve his way out of trouble, while the 5-foot-7 Nishioka will need to work much harder to win his service games. Nishioka won a title in Atlanta last month but then suffered first-round losses to players outside the top 80 in back-to-back tournaments. His lack of power makes it difficult for the 52nd-ranked Nishioka to keep pace with top-10 players like the seventh-ranked Hurkacz, as evidenced by Nishioka’s 4-26 career record against top-10 players.

Jasmine Paolini (-225) vs. Anastasia Potapova

Paolini’s runs to the finals of the French Open and Wimbledon overshadowed her hard-court success early in 2024, but the Italian’s breakout began well before the clay and grass portions of the year, as she won a Masters 1000 title in Dubai. Since the start of that tournament, she’s 28-9 overall, and the world No. 5 should keep adding to her success against the 44th-ranked Potapova, who has had a disappointing season. After climbing to 21st in the rankings last June, the 23-year-old Russian has tumbled back down to 44th while posting a pedestrian 20-17 record in 2024. Potapova beat Paolini at Indian Wells despite dropping the second set 6-0 but has gone into a tailspin with a 10-12 record since that match, while Paolini has proceeded to play the best tennis of her career.

Honorable Mention

Andrey Rublev (-300) vs. Zhizhen Zhang

Cincinnati Open Tennis Predictions: Value Bets

Diana Shnaider (-165) vs. Ashlyn Krueger

Shnaider has been one of the top performers on the WTA Tour over the past couple months, going 18-3 in her last 21 matches while claiming two titles over that span and knocking off Gauff en route to the semifinals of the Canadian Open last week before falling to eventual champion Jessica Pegula. The 20-year-old Russian is unlikely to slow her roll against fellow 20-year-old Krueger, who came into this tournament just 21-20 on the year. Krueger got through qualifying then upset Olympic silver medalist Donna Vekic in Vekic’s first hard-court match since March, but backing that effort up will be tough for the American against the in-form Shnaider.

Flavio Cobolli (-165) vs. Luciano Darderi

Cobolli has had a terrific hard-court swing to get his ranking up to a career-best 31st, as the 22-year-old Italian has gone 6-2 since the end of the clay-court season, including top-20 wins over Ben Shelton, Felix Auger-Aliassime and Tommy Paul. Fellow 22-year-old Italian Darderi is ranked just three spots behind Cobolli at No. 34, but Darderi has a distinct preference for clay, as he came into this tournament without an ATP Tour-level hard-court win in his career. Darderi got that first win against Alejandro Tabilo in the opening round here, but Cobolli is coming off a much more impressive first-round win over Paul. In what will be the first official meeting between these Italian compatriots born less than three months apart, Cobolli has the distinct edge due to the court conditions.

Honorable Mention

Arthur Fils (+100) vs. Brandon Nakashima