This article is part of our Tennis Picks series.
The first round of Wimbledon rolls on Tuesday from the grass courts of the All England Club in London. This could be a tough day for British men, including an all-time great who is a shadow of his former self at this point. The top women's seed has a rough welcome to the tournament against a former top-five player, while a former world No. 1 is in good position to advance.
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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 overwhelming favorites, while the Value Bets section recommends enticing options in matchups that are considered closer to toss-ups.
Wimbledon Picks: Upset Alert
Sofia Kenin (+1000) vs. Iga Swiatek
Kenin hasn't been able to recapture the form that helped her reach No. 4 in the world back in 2020, but the 25-year-old American shows glimpses of it every now and again. She played arguably her best match of 2023 in last year's Wimbledon first round to upset Coco Gauff, and Kenin will have her eye on another upset bid in the first round this year. Grass is by far Swiatek's worst surface, as the world No. 1 is just 9-4 in her career at Wimbledon, and Swiatek may require an adjustment period to grass in what will be her first match since winning the French Open on clay. Kenin was able to hang with Iga for a set in the first round of this year's Australian Open before falling 7-6 (2), 6-2, and the gap between them is far smaller on grass.
Thanasi Kokkinakis (+215) vs. Felix Auger-Aliassime
Both of these 6-foot-4 players are capable of dominating their service points, especially on grass, so this match could come down to which player steps up on their few break point opportunities or in tiebreaks. Auger-Aliassime hasn't handled such pressure well in the last couple years, as he has crashed out in the first round of the past two Wimbledon championships. Health is a concern for both players, as each pulled out of a grass-court tune-up event due to injury in the lead-up to Wimbledon.
Honorable Mention
Kei Nishikori (+200) vs. Arthur Rinderknech
Wimbledon Odds: Lock It In
Tomas Machac (-300) vs. Andy Murray
It's amazing that Murray is playing at all less than two weeks after undergoing surgery to remove a spinal cyst, but this appearance looks like a ceremonial one with the British legend looking to take Centre Court one last time before riding off into the sunset; Murray reportedly plans to retire after the Olympics later this summer. While the 37-year-old Murray's in the twilight of his career and just 6-12 in 2024, the 23-year-old Machac is ascending. Machac has climbed into the top 40 with an 18-10 record in 2024, including a pair of wins over Murray.
Katerina Siniakova (-400) vs. Marina Stakusic
Siniakova's game is a nice fit for grass, as the outstanding doubles player loves to get to the net. She's ranked a respectable 36th in singles but fifth in doubles, and the Czech has posted an impressive 6-1 record this grass-court season, including top-20 wins over Emma Navarro and Qinwen Zheng. Like many players heading into this tournament, Siniakova withdrew from a lead-up event with an injury, but the majority of such withdrawals are precautionary, though Aryna Sabalenka and Victoria Azarenka have proven to be unfortunate counterexamples due to their respective shoulder injuries. Stakusic did well to qualify into her first Grand Slam main draw here, but the 19-year-old Canadian has yet to establish herself as a competitive WTA Tour player and is ranked 164th.
Honorable Mention
Alexei Popyrin (-285) vs. Thiago Monteiro
Wimbledon Predictions: Value Bets
Thiago Seyboth Wild (+130) vs. Paul Jubb
Seyboth Wild doesn't have much grass-court experience, but the 24-year-old Brazilian's flashy shot-making gives him the ability to succeed on all surfaces. The Roger Federer lookalike has had a breakout season in 2024, briefly entering the top 60 for the first time before falling back to his current ranking of No. 74. He pushed Andrey Rublev to a fifth-set tiebreak at the Australian Open before notching top-20 wins over Karen Khachanov in Indian Wells and Taylor Fritz in Miami. Jubb's favored in this match after a strong run to the semis in Mallorca, which included a win over Ben Shelton, but the Brit is the far less accomplished of these 24-year-olds. Jubb didn't have an ATP Tour win prior to Mallorca and is ranked No. 201.
Caroline Wozniacki (-165) vs. Alycia Parks
Wozniacki struggles to generate power at this stage of her career, so playing on the fast grass should help the former world No. 1, and she notched two top-40 wins on grass at the Bad Homburg Open before pulling out with a knee injury. Having already retired and returned to play previously, the 33-year-old Wozniacki will do all she can to play at what's likely to be one of her last appearances at Wimbledon. Parks has the substantial edge in power, but the 23-year-old American qualifier has struggled badly with consistency en route to a 9-16 record in 2024 which has dropped Parks to 121st in the rankings. This is a nice stylistic matchup for the counterpunching Wozniacki, who can redirect Parks' power effectively and bait her inaccurate opponent into errors.
Honorable Mention
Lauren Davis (+125) vs. Camila Osorio
