U.S. Open Day 5 preview and best bets: All aboard the Serena Williams bandwagon

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Ricky Dimon

Tennis

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Since graduating from Davidson (The College That Stephen Curry Built), I have been writing about sports -- just about any and all you can think of! -- and coaching tennis in Atlanta, GA. Beyond the four major sports, I am an avid tennis fan and cover the ATP Tour on a daily basis. If I'm not busy writing, you can generally find me on a tennis court or traveling the world wherever a sporting event takes me. For Ricky Dimon media enquiries, please email contact@pickswise.com.
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The Serena Williams storyline at the 2022 U.S. Open has gone from a ceremonial goodbye to title contention in a New York minute. That’s what happens when you don’t win a single match for more than an entire year and then suddenly upset the No. 2 player in the world. Williams accomplished that feat in front of a raucous Arthur Ashe Stadium crowd on Wednesday night, sending her through to the third round. The 23-time Grand Slam champion will be back in action on Friday along with two Americans of different generations in Coco Gauff and Madison Keys.

There is plenty to choose from on another jam-packed day of tennis in New York, so let’s check out my favorite plays. We could not be more straightforward with today’s picks–three money line winners. No complications. No nonsense. Just winners. I am 6-3 through three days, so let’s keep it rolling!

Serena Williams ML over Ajla Tomljanovic (-149)

Somewhat surprisingly, Williams’ odds did not entirely skyrocket following Wednesday’s heroics. She is only the sixth favorite to win the title (+1400 at DraftKings) and isn’t much of a favorite over Tomljanovic on Friday. I’m not going to go crazy and pick her to win the tournament just yet even at that price, but you have to like the fact that the odds haven’t gone through the roof. The value is still there; getting her at -149 against Tomljanovic is a great opportunity. Williams played incredibly well against Kontaveit and with two wins under her belt she should only be getting better and better. After all, she has barely played tennis in a year. Every victory is hugely important for her progress. Tomljanovic is no slouch, but let’s just say she is not exactly known for her mental toughness in high-pressure situations. That is exactly what she will face in this one, as Kontaveit did not only against Williams but also against the crowd on Wednesday night. Back the GOAT to go full steam ahead.

Coco Gauff ML over Madison Keys (-146)

Gauff may be the favorite, but the pressure is on Keys. After all, she is the much older player (27 to 18) and won’t want to lose to a younger compatriot at home on tennis’ biggest stage. Plus, although time is not exactly running out on Keys (just ask Williams, who is 40!), she also isn’t getting any closer to her prime. Her chances to finally win a Grand Slam title aren’t improving. As for Gauff, it’s only a matter of time before she lifts a slam singles trophy for the first time. The teenager finished runner-up at the French Open this spring and is already the No. 1 doubles player in the world. Moreover, Gauff has been bullying opponents this week while Keys needed a third-set tiebreaker to get past Camila Giorgi on Wednesday.

Jack Draper ML over Karen Khachanov (-144)

This is a tale of two players going in opposite directions. Khachanov may be the higher-ranked player, but Draper should be an even bigger favorite. The Brit is only 20 years old and hasn’t been playing a full schedule; he is much better than his No. 53 ranking suggests and he is especially playing like it right now. Draper is coming off quarterfinal appearances in Montreal and Cincinnati, and so far in New York he has erased both Emil Ruusuvuori and Felix Auger-Aliassime in easy straight sets. Those are tough opponents for the first two rounds, too. Meanwhile, Khachanov’s peak ranking is No. 8 but he is now 31st. The 26-year-old Russian had been just 6-6 in his last 12 matches prior to this tournament, so confidence is lacking. Draper should be a safe choice.

The Pickswise tennis handicappers are on hand throughout the entire tennis season, bringing you the best free expert Tennis Predictions and Picks from top events including the Australian Open, French Open, Wimbledon and U.S. Open.

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