This article is part of our Tennis Picks series.
The first round of Wimbledon continues Tuesday from the grass courts of the All England Club. After all the off-court drama surrounding who won't be playing in this tournament, we're finally shifting our focus onto those competing inside the lines. Some prominent day two matches feature clashes between players looking to utilize extensive grass-court experience against those who are still learning to master the surface. On the men's side, one of Great Britain's brightest young stars will look to thrill the local fans while a pair of Americans find themselves on opposite sides of potential upsets. In the women's singles, a pair of top-10 seeds should take care of business while a former champion faces a stiff first-round test. All match odds below are taken from DraftKings Sportsbook, but you can sometimes find more favorable odds on some of these matches by checking other mobile sportsbooks such as FanDuel, BetMGM or Caesars.
Grass-court form can be notoriously hard to judge given the rapid transition from the slower clay to the faster grass, but recent results on all surfaces coupled with historic grass-court results and a look at playing style can usually provide an accurate approximation of a player's ability on this surface. The stakes are highest at the Grand Slams, and the men play best-of-five set matches rather than the best-of-three seen at other ATP Tour events. Conditions vary from tournament to tournament, and even from day to day, but the fast pace and low bounces of grass generally favor more aggressive players, and especially those that possess big serves. Using this context 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 considered overwhelming favorites, while the Value Bet section recommends enticing options in matchups that are considered closer to toss-ups.
Upset Alert
Maxime Cressy (+265) vs. Felix Auger-Aliassime
Cressy's game is tailor-made for Wimbledon, as the American employs an old-school serve and volley style. This will be the main draw Wimbledon debut for the 25-year-old Cressy, but he has racked up some valuable grass court experience this month, posting a 7-3 record on the surface, including a run to the final of Eastbourne last week. Cressy's strong run on the surface includes winning 15 of 23 sets, with four of the eight lost sets coming in tiebreaks. All the pressure will be on Auger-Aliassime, who reached the quarterfinals here last year, and this match could well come down to a few key points, on which Cressy should be playing more freely as the underdog.
Mikhail Kukushkin (+205) vs. Jenson Brooksby
Brooksby made a name for himself at last year's US Open, but the 21-year-old American has struggled to translate his unorthodox style effectively to surfaces besides hard courts up to this point. He's just 1-3 on grass this year, and the lone win came against 171st-ranked Jesper De Jong. Kukushkin's ranked in the same range as De Jong at No. 164, but the 34-year-old veteran will be able to lean on a significant edge in grass-court experience in this match, which will be Brooksby's Wimbledon debut. Conversely, this will be Kukushkin's 10th Wimbledon main draw appearance; he got here the hard way, grinding his way through three victories in qualifying.
Honorable Mention:
Karolina Muchova (+275) vs. Simona Halep
Lock It In
Jack Draper (-290) vs. Zizou Bergs
Draper isn't a household name yet, but it's likely just a matter of time before the next big thing in British men's tennis becomes one. The 20-year-old has been groomed for success from a young age as the son of former Lawn Tennis Association chief executive Roger Draper, and Jack's starting to live up to his potential judging by his semifinal run in Eastbourne. He used his big serve and forehand to defeat Brooksby, Diego Schwartzman and British countryman Ryan Peniston each in straight sets before falling in three to Cressy. The 94th-ranked Draper has a favorable first-round draw against 23-year-old Belgian Zizou Bergs, who just won a challenger event on grass but is still ranked just 146th in the world.
Karolina Pliskova (-285) vs. Tereza Martincova
Pliskova has gone just 2-2 on grass leading up to this tournament, but the 2021 Wimbledon runner-up has played a difficult schedule on the surface, beating Kaia Kanepi and Bianca Andreescu before losing to Coco Gauff and Katie Boulter. The latter loss is a little suspect, but Pliskova can take solace in knowing that Boulter also beat Martincova at that same tournament as part of a three-match losing streak that Pliskova's 61st-ranked countrywoman from the Czech Republic brings into this match. Pliskova's the far more accomplished grass-court player, and the No. 6 seed's 2-0 head-to-head record against Martincova includes a 6-3, 6-3 win at last year's Wimbledon.
Honorable Mention:
Sam Querrey (-450) vs. Ricardas Berankis
Value Bet
Jessica Pegula (-150) vs. Donna Vekic
Vekic is an uncomfortable first-round draw for Pegula, but the eighth-seeded American is unequivocally the better player at this stage of their respective careers. The 25-year-old Croatian has made the Round of 16 or better at every Grand Slam in her career, but Vekic has dropped to No. 82 in the world and is just 6-7 in her career at Wimbledon. Pegula hasn't played a match since her quarterfinal loss to Iga Swiatek at the French Open, but she has been a tough out all year. She's 23-10 since the start of the Australian Open, where Pegula also made the quarterfinals.
Holger Rune (+110) vs. Marcos Giron
The ascendant Rune's a nice value as a modest underdog against the 65th-ranked Giron. Rune is seeded No. 24 here coming off a quarterfinal run at Roland Garros. The 19-year-old Dane has dropped both of his grass-court matches since then, while Giron has gone 2-3 on grass this month, but there's little question Rune's baseline level is already substantially higher regardless of surface. Rune will be amped up for his Wimbledon debut, but playing on one of the outer courts should help him manage the nerves better against the 28-year-old American.
Honorable Mention:
Denis Kudla (-115) vs. Lorenzo Sonego
