A day later Emma Raducanu was born. About 21 years separate Williams, 40, and Raducanu, 19, and generations apart. It was unlikely that they would ever face each other on a court as professionals. But on Monday night, undefeated Williams and 10th seed Raducanu will square off in the opening round of the Western & Southern Open in Cincinnati, Ohio. Their first meeting is very likely to be their last. Less than a week after Williams announced that she had “evolved away from tennis” and that her retirement was imminent, the countdown continues. After losing to a clean-cut Belinda Bencic in her second-round match at the National Bank Open in Toronto, Williams was overcome with emotion, barely holding back tears in her on-court interview. He’ll play in Cincinnati, then the US Open, and then he expects to be done. Raducanu will be the second youngest opponent of Williams’ career. Despite her continued presence on the tour, Williams has not played against many top players of the current generation, only four of the current top 11 ranked players have ever faced her. As her peers reacted to her retirement announcement earlier in the week, a common sentiment shared by many players, particularly Iga Swiatek and Coco Gauff, was regret that they never got the chance to play against her. The best of our sports journalism from the past seven days and a heads-up of the weekend’s action Privacy Notice: Newsletters may contain information about charities, online advertising and content sponsored by external parties. For more information, see our Privacy Policy. We use Google reCaptcha to protect our website and Google’s Privacy Policy and Terms of Service apply. “A little sad because I’ve always wanted to play her,” Gauff said. “So hopefully my draw in Cincinnati or the US Open or even here can work out so we can play each other. Because that’s just one of my goals.” For so long, players were desperate to avoid Williams. Now in the final weeks of her career, many are hoping to cross Williams off their list, a chance Raducanu took. “He’s accomplished so much,” Raducanu said in Toronto. “And to see her in that US swing is really inspiring. She keeps playing because she obviously likes the game. And I think the longevity of a career is something that many of the players, and myself in particular, aspire to achieve as well.” The countdown hasn’t just begun for Williams. Cincinnati will also mark Raducanu’s final match before she returns to New York to defend her US Open title and the 2,000 points she earned. She has constantly emphasized that she is not bothered by her current position, but the increased pressure is natural. Monday night, however, will be a rare occasion over the past year where the majority of focus and attention will be on the player beyond the net from Raducanu, perhaps an opportunity for her to swing freely against to an opponent who has been a legend ever since. the day Radukanou was born.