Second-round play at Wimbledon continues Thursday on the grass courts of the All England Club in London. A pair of former top-five players will try to turn back the clock in upset bids against top-10 seeds, while a few players that built momentum during the French Open will look to keep rolling despite the switch in surface from clay to grass.
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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
Sofia Kenin (+471) vs. Amanda Anisimova
Kenin has fallen precipitously from her 2020 high, but the 27-year-old American still has the talent that got her to No. 4 in the world six years ago, and she has still produced some big wins in recent years, including a Wimbledon upset of Coco Gauff in 2023. Kenin has a chance to upset another top-10 American compatriot this year, facing the fellow Russian-American Anisimova. The sixth-seeded Anisimova has been hampered by a wrist injury for the last couple months and has beaten only one top-100 player over the past three months while posting a pedestrian 4-3 record in her last seven matches. Kenin has dropped to 105th in the rankings but built some much-needed confidence with a top-50 win over Petra Marcinko in the first round. Kenin has absorbed Anisimova's power effectively in their previous matchups and leads their head-to-head 2-1.
Karolina Pliskova (+288) vs. Iga Swiatek
Prior to winning Wimbledon last year, Swiatek had a reputation as an underwhelming grass-court player, and she has looked shaky on the surface in limited action in 2026. She lost her only grass-court match in the lead-up to Wimbledon against Emma Navarro at the Bad Homburg Open, and Swiatek was pushed to three sets in the first round here by 79th-ranked Taylor Townsend while facing 12 break points and double faulting nine times in a poor serving performance. Pliskova is capable of capitalizing on another subpar Swiatek serving effort, as the 73rd-ranked Czech still has one of the most effective serves on the WTA Tour herself, and the former world No. 1 wasn't broken in the first round against 54th-ranked compatriot Tereza Valentova. The 34-year-old Pliskova is on the backside of her career, but she has enjoyed a quietly strong season, with a 20-9 record and five top-30 wins.
Honorable Mention
Matteo Berrettini (+182) vs. Arthur Fils
Wimbledon Tennis Odds: Lock It In
Zizou Bergs (-187) vs. Jaime Faria
Bergs is in fine grass-court form, as he won the tune-up in Eastbourne in the week leading up to Wimbledon, then defeated 27th-seeded Ugo Humbert in the first round in a five-set rematch of the Eastbourne championship match. The 37th-ranked Belgian narrowly missed getting a seed here himself, and his willingness to get forward makes Bergs an effective grass-court player. The 98th-ranked Faria is a clay-court specialist who didn't have a grass-court main-draw win in his career prior to his first-round victory over 90th-ranked Sho Shimabukuro. Faria got through qualifying here to make the main draw, but he also had a loss to 189th-ranked Zhizhen Zhang at the Challenger level in his only grass-court event prior to Wimbledon this year.
Flavio Cobolli (-288) vs. James Duckworth
Cobolli has been one of the top all-court performers on the ATP Tour over the past year, and the 2025 Wimbledon quarterfinalist is riding high after breaking through to the final of the French Open a few weeks ago. The 10th-ranked Italian should keep rolling against the 79th-ranked Duckworth, who has a 4-11 record in ATP Tour-level main draw matches this year. Duckworth is just 14-22 on grass in his career, including 4-8 at Wimbledon.
Honorable Mention
Alexander Bublik (-362) vs. Kyrian Jacquet
Wimbledon Tennis Predictions: Value Bets
Quentin Halys (-116) vs. Marcos Giron
Halys is trying to reach the third round here for the third time in four years, and the 95th-ranked Frenchman created that opening for himself with a four-set first-round win over 32nd-seeded recent French Open semifinalist Matteo Arnaldi. Halys is a strong offensive player with suspect movement, so the quick and slippery conditions on grass help maximize his strengths and minimize his weaknesses. The 92nd-ranked Giron is a grinder with a ceiling to his game. He has lost in the second round of Wimbledon in each of the past five years and has a 6-6 career record at the All England Club. The 32-year-old American hasn't been past the second round of a Grand Slam or Masters 1000 event in over a year dating back to a third-round loss at the 2025 Italian Open, while Halys reached the fourth round of the Miami Open and third round of the French Open this year.
Diana Shnaider (-139) vs. Liudmila Samsonova
Shnaider is 6-1 in her last seven Grand Slam matches, as she's coming off a breakthrough semifinal performance at the French Open. The arrow is pointing up for the 22-year-old Russian, while the opposite is true for the 27-year-old Samsonova, who was a top-25 staple for the past few years but has dropped out of the top 40 with a 9-16 record in 2026. Samsonova has hit herself out of many matches this year with errors and generally lacks a plan B when her timing is off. The 15th-seeded Shnaider can produce plenty of power herself, but the young lefty has also demonstrated the ability to change tactics and adapt th the flow of matches, unlike Samsonova. Shnaider has a 2-0 career head-to-head edge over Samsonova.
Honorable Mention
Zachary Svajda (+146) vs. Kamil Majchrzak
