Two wildcards face off in the first round of the US Open in the early hours of Monday morning, when Venus Williams takes on Sofia Kenin.
With seven Grand Slam titles to her name, Williams is a legendary figure in the sport and will almost undoubtably be inducted into the International Tennis Hall of Fame when she retires.
At 46 years of age it is impressive she is still competing on the WTA Tour, although she has failed to win a singles match this year and her awarding of a wildcard for the US Open has been met with mixed reviews.
Kenin, who at 101st is 501 places higher in the WTA rankings than Williams, was also handed a wildcard for the New York spectacle and her younger legs should have more than enough to advance into the second round.
Venus Williams v Sofia Kenin Tips Summary
Best Bet - Sofia Kenin to win and under 19.5 games @ 21/20
Alternative Bet - Sofian Kenin to win first set 6-2 @ 7/2
Bet Builder - Sofia Kenin to win 2-0, under 0.5 tie breaks, Sofia Kenin 5+ double faults & Venus Williams 3+ double faults @ 23/4
Venus Williams v Sofia Kenin Prediction
Best Bet: Sofia Kenin to win and under 19.5 games @ 21/20
The decision to hand Williams a wildcard has split opinion, with former world number one Yevgeny Kafelnikov critical of the decision while Andy Roddick backed his fellow American.
Whether you agree with the seven-time Grand Slam champion competing in the US Open or not, the 46-year-old will take to the court for the first round, but it could be a short-lived time for her in the singles.
Williams has yet to win a singles match in 2026, losing all 11 contests and winning just four sets in the process, and her advancing years have clearly caught up with her.
It is seven years since the US legend managed to make it past the first round in New York and it is hard to look past anything other than a comfortable win for Kenin.
While no great shakes herself, Kenin has managed to win six matches this year, the most recent of those victories coming against Eva Lys at the Cincinnati Open.
Six of Williams' last 10 defeats have seen fewer than 20 total games and this looks like a perfect opportunity for Kenin to breeze into the second round.
Alternative Bet: Sofian Kenin to win first set 6-2 @ 7/2
A quick start to this match will set Kenin on her way to an easy win and there looks to be good value in backing her to claim the first set 6-2.
Williams has lost the first set by this scoreline in three of her last five appearances, including in her last outing against Emiliana Arango at the Cincinnati Open.
Venus Williams v Sofia Kenin Bet Builder Tip
Sofia Kenin to win 2-0
Under 0.5 tie breaks
Sofia Kenin 5+ double faults
Venus Williams 3+ double faults
Pays 23/4
Williams has lost five of her last six matches in straight sets and another chastening loss looks to be on the cards against Kenin.
There has not been a tie break in Kenin's last four matches or Williams' last three contests.
Kenin can struggle on serve and she has made at least five double faults in her last five singles matches.
Williams also has her issues on serve and has made at least three doubles in 10 of her 11 matches this year.
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Key Match Stats
Venus Williams has not won a singles match in 2026
The seven-time Grand Slam champion last won a single match in July 2025
Sofia Kenin has won six singles matches this year
The 2020 Australian Open champion has reached the second round of the US Open in two of the last three editions
Williams has not made it past the first round in New York since 2019
This will be the first meeting between the two players
Read more tennis betting tips and predictions on site.
This article was written by a partner sports writer via Spotlight Sports Group. All odds displayed on this page were correct at the time of writing and are subject to withdrawal or change at any time.
