In what could be the penultimate tournament of her career, 23-time grand slam champion Serena Williams takes on US Open champion Emma Raducanu in Cincinnati.
Potentially two more tournaments to go before a legend of the sport retires in the form of Serena Williams.
Williams began her farewell tour in Toronto where she went out in the second round to Belinda Bencic and will look to make a bigger impression in Cincinnati.
However an intriguing task awaits in her opening match in Ohio as she will take on US Open champion Emma Raducanu in the opening round.
Raducanu enters the match in uninspiring form having reached the quarter-finals in Washington before an opening round exit against Camila Giorgi in Toronto.
It will be interesting how this match fairs as Williams gets a taste of facing the younger generation before she departs the sport.
That match is in a packed part of the draw where the winner of that match will play the winner of Kaia Kanepi and Victoria Azarenka.
There is also a huge match between Bianca Andreescu and Camila Giorgi with the winner taking on seventh seed Jessica Pegula in the second round.
As for Serena’s sister, Venus Williams, she hasn’t fared much better with her draw as she takes on 14th seed Karolina Pliskova in her opening round.
Also in this section of the draw is fourth seed Maria Sakkari who takes on either a qualifier or Alison Van Uytvanck.
Other highlights of the bottom half of the draw will see Sofia Kenin take on Shelby Rogers while Amanda Anisimova takes on Daria Kasatkina.
Naomi Osaka is also in the bottom half of the draw where she takes on Shuai Zhang.
Meanwhile in the top half of the draw Iga Swiatek will look to bounce back after an early exit in Toronto as she takes on Sloane Stephens or Alize Cornet in her opening round.
Other exciting matches in the top half of the draw sees Simona Halep take on Karolina Muchova while Beatriz Haddad Maia takes on Jelena Ostapenko.
Here is the full Women’s singles draw with Serena Williams expected to play on Monday night:
