This article is part of our Tennis Picks series.
Wimbledon 2025: Top Upsets, Locks, and Value Bets for Opening Monday
The first round of Wimbledon begins from the grass courts of the All England Club in London. Both halves of one of tennis' power couples could have trouble getting through the opening round, while a few doubles specialists in the women's game could be outclassed by higher-ranked singles players.
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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
Valentin Royer (+270) vs. Stefanos Tsitsipas
Tsitsipas has been in freefall recently, failing to string together multiple wins at any of his last four tournaments. That poor stretch includes the French Open, where Tsitsipas had made at least the Round of 16 in six consecutive years prior to falling in the second round to 167th-ranked Matteo Gigante. The No. 24 seed has never been especially comfortable on grass, with three first-round losses at Wimbledon and just a 9-7 record here in his career. The 112th-ranked Royer has had a chance to get used to the conditions, winning three qualifying matches to make the Wimbledon main draw for the first time. Given the fragile state of Tsitsipas' backhand and mental game, it's tough to pencil him in as a heavy favorite against any opponent, especially on grass.
Lulu Sun (+160) vs. Marie Bouzkova
Sun reached the quarterfinals in her Wimbledon main draw debut last year, and her high-risk style can be very rewarding on grass when her timing is right. Bouzkova's also a former Wimbledon quarterfinalist, having gotten there in 2022, but she has been past the second round only one other time in five main-draw appearances and has a 17-23 overall record in Grand Slams. Bouzkova's a good doubles player whose volleying ability works well on grass, but Sun has a significant edge in power from the baseline, so Bouzkova may find it difficult to consistenly work her way to net. Sun has a one-spot edge in the rankings at No. 46, and this match will ultimately hinge on how well she's timing the ball.
Honorable Mention
Lloyd Harris (+160) vs. Zizou Bergs
Wimbledon Tennis Odds: Lock It In
Marketa Vondrousova (-275) vs. McCartney Kessler
Vondrousova won Wimbledon in 2023 and is in strong grass-court form, having defeated world No. 1 Aryna Sabalenka en route to a grass-court title in Berlin just over a week ago. The Czech lefty is one of the best grass-court players in the world when she's healthy, and she finally seems to be finding a groove after injuries have limited her for much of the past two years, resulting in her underwhelming current ranking of No. 73. Kessler just snagged a seed here at No. 32, but the 25-year-old American is just 1-5 in Grand Slam matches in her career. She also won a title during this grass-court season but didn't face a top-20 opponent on her path to doing so in Nottingham.
Qinwen Zheng (-185) vs. Katerina Siniakova
Zheng's 2-3 career record at Wimbledon can be attributed primarily to a lack of experience on grass, as the No. 5 seed has a well-rounded game that should work well anywhere. She has already made the quarterfinals or better at all three other Grand Slams at age 22. Siniakova focuses more on doubles than singles, as the top-ranked doubles player is just No. 78 in singles and has a 28-42 career record in Grand Slam matches. You have to go back to Wimbledon 2021 to find the last time Siniakova made it past the second round in a Grand Slam, and she simply lacks the baseline proficiency to hang in rallies with a player of Zheng's caliber.
Honorable Mention
Holger Rune (-350) vs. Nicolas Jarry
Wimbledon Tennis Predictions: Value Bets
Olga Danilovic (-140) vs. Shuai Zhang
Danilovic is ranked 39th and ascending, having made the Round of 16 at the Australian Open and third round of the French Open. The Serbian lefty has plenty of power, giving her the tools to excel on grass, though this will be only her second time in the Wimbledon main draw at age 24. While Danilovic is just hitting her prime, Zhang's best tennis is behind her, as the 36-year-old focuses primarily on doubles at this stage and had a 24-match singles losing streak that stretched into late 2024. Zhang has lost her first-round match in eight of 10 previous singles main draw appearances at Wimbledon.
Katie Boulter (+140) vs. Paula Badosa
This matchup is one of the biggest draws of the first round, as the 41st-ranked Boulter is just three ranking spots behind Emma Raducanu for the top spot among British women, while the ninth-seeded Badosa is a household name in the women's game. Grass has been Boulter's best surface, as two of her three career titles have come on grass, and she has advanced to the third round of Wimbledon in two of the previous three years. Wimbledon is the only Grand Slam at which Badosa has yet to reach the quarterfinals in her career, and Badosa's extensive injury history adds an extra layer of discomfort on this surface, which tends to be especially slippery in the early rounds before getting tamped down near the baseline. Throw in the crowd support in Boulter's corner, and this clash between big hitters is likely to come down to the wire, much like their only previous match: a 4-6, 7-5, 6-4 Badosa win at last year's French Open.
Honorable Mention
Harriet Dart (-125) vs. Dalma Galfi
