The first round of Wimbledon begins Monday on the grass courts of the All England Club in London. A highly ranked underdog will try to overcome his previous lack of success on grass, while a women's seed coming off a breakout French Open run looks to keep building momentum Monday.
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All men's singles matches at Grand Slams such as Wimbledon are best of five sets, while women's singles matches are best of three sets. A mix of players' previous grass 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 favorites, while the Value Bets section recommends enticing options in matchups that are considered closer to toss-ups.
Wimbledon Tennis Picks: Upset Alert
Casper Ruud (+174) vs. Hubert Hurkacz
Ruud is just 3-5 at Wimbledon in his career and has a style that's much better suited for slower courts, but the three-time Grand Slam finalist and current world No. 12 is a nice value as a first-round underdog against the 95th-ranked Hurkacz, who is just 10-13 this year, including a 1-2 record on grass. Hurkacz reached the Wimbledon semifinals in 2021, but he's just 4-4 in his last eight matches at the All England Club and hasn't been past the second round of a Grand Slam since the 2024 French Open. With injuries sapping Hurkacz's effectiveness in recent years, it's hard to view him as a clear favorite against a player of Ruud's caliber, regardless of the surface. Ruud has a 3-1 career head-to-head advantage, and while Hurkacz gets more free points on serve, Ruud can get on the front foot quickly in any forehand-to-forehand rallies thanks to the Norwegian's major edge in power off that wing.
Oleksandra Oliynykova (+498) vs. McCartney Kessler
Kessler has been just about the definition of middling this year, as the 57th-ranked American has a 16-15 overall record, including a 2-3 mark on grass. Two of those three grass-court losses came against opponents ranked outside the top 100. She's just 4-9 in Grand Slam main-draw matches in her career and has a 0-2 record at Wimbledon. Oliynykova actually has a four-spot edge in the rankings over Kessler, but the 25-year-old Ukrainian lacks experience on grass. This will be Oliynykova's Wimbledon debut, and the clay-court specialist lost 6-0, 6-2 to 587th-ranked Sofia Johnson in her only grass-court match this year, but that ugly result doesn't mean that Oliynykova is completely incapable of playing on grass. Given Kessler's underwhelming Grand Slam resume, the gap between these two players on grass isn't nearly as large as the odds suggest.
Honorable Mention
Marco Trungelliti (+287) vs. Martin Damm
French Open Tennis Odds: Lock It In
Andrey Rublev (-195) vs. Roman Safiullin
Rublev has reached at least the fourth round in three of his last four Wimbledon appearances, and the 12th-seeded Russian has made the third round or better in 17 of his last 19 Grand Slam appearances overall. His big serve and forehand should help Rublev control play against the 127th-ranked qualifier Safiullin, who hasn't won a main-draw match on the ATP Tour this year. Even including Safiullin's surprising quarterfinal run at Wimbledon in 2023, he is just 11-15 in Grand Slam matches in his career.
Cameron Norrie (-169) vs. Michael Zheng
Norrie retired in the first round of the French Open due to a rib injury, but he returned to action at Queen's Club earlier this month, suggesting that the 26th-seeded Brit has regained health heading into his home slam. The crafty lefty has thrilled the London crowd with multiple deep runs at Wimbledon, reaching the semifinals in 2022 and quarterfinals in 2025. As long as Norrie's anywhere near full effectiveness, he shouldn't have too much trouble taking care of business against the 143rd-ranked qualifier Zheng, who has won only one match at the main-draw level on the ATP Tour in his career.
Honorable Mention
Solana Sierra (-188) vs. Anna Bondar
French Open Tennis Predictions: Value Bets
Maja Chwalinska (-116) vs. Mananchaya Sawangkaew
Even if you view Chwalinska's run to the French Open final as a fluke, the 24-year-old Pole is still a better player than the 164th-ranked Sawangkaew, who will be making her Grand Slam main draw debut at age 23 after getting through qualifying here. Chwalinska has jumped up to No. 21 in the rankings, and she has found success at all levels of competition this year with a 29-10 overall record. Her crafty game certainly seems to fit best on clay, but there's no substitute for the confidence Chwalinska developed from her Cinderella run at Roland Garros, and she should get some mileage out of her lefty slice serve on grass as well.
Dino Prizmic (-144) vs. Adam Walton
The 20-year-old Prizmic isn't a household name yet, but he's quickly moving in that direction. He turned heads with a win over Novak Djokovic in Rome and had a two-set lead against Joao Fonseca before coming up short at the French Open, showing that the young Croatian is ready to go toe-to-toe with some of the biggest names in the sport on big stages. He's just getting started on grass, with a 0-1 career record on the surface, but the gap in ability between the 81st-ranked Prizmic and the 92nd-ranked Walton is far greater than their 11-spot difference in rankings suggests. Walton has a 21-41 career record on the ATP Tour, including 5-10 this year, and the 27-year-old Aussie has never advanced past the second round of a Grand Slam.
Honorable Mention
Arthur Rinderknech (-163) vs. Oliver Tarvet
