Reunited: Close friends Serena Williams and Caroline Wozniacki share heartwarming moment at Sports Illustrated party

Sunday, 03 May 2026 at 00:30

Players, rivals but most importantly friends as Caroline Wozniacki reunited with her good friend Serena Williams in a heartwarming reunion for those who of course watched them during their time on the court.

During an event organised by Sports Illustrated in Miami, Williams and Wozniacki met up. The Dane shared several photos of their moment together. Accompanied by the simple message: "So happy to have seen my best friend again."

Often when they retire from the sport albeit both technically haven't yet, rivals become friends like Nadal and Federer or they don't tend to see much of each other again and for Wozniacki and Williams, they fit the latter in not seeing much of each other but also the former too as when they do reunite it is heartwarming.

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The two players faced each other 11 times during their careers. Williams dominated the head-to-head with 10 wins, while Wozniacki only won once. In the Quarter-Finals in Miami in 2012 no less ironically where they reunited.

Both are a bit of a cloud when it comes to retirement. Wozniacki has had another child albeit has in the past indicated she is unlikely to return after her ill-fated comeback prior to becoming a mum again while it has gone semi quiet on the Williams front after her decision to enter the doping protocol.

Her sister Venus still at 45 defies tennis belief by still playing on but whether Serena will join her is another matter. But good to see two icons of the sport back together.

Serena Williams and Caroline Wozniacki at the Sports Illustrated Race Weekend Party

“So happy we got to catch up with my bestie” ❤️

(via Caroline’s IG) pic.twitter.com/H6HXNNzYg5
— The Tennis Letter (@TheTennisLetter) May 2, 2026

Samuel GillEditor-in-Chief

Samuel Gill is the Chief Content Officer (CCO) of TennisUpToDate.com, a role he has held since 2020. He is responsible for editorial governance across the platform, including setting content standards, overseeing accuracy and consistency, and guiding long-term editorial strategy. Since joining, he has contributed more than 10,000 articles and editorial pieces across the TennisUpToDate network, playing a central role in the daily operation and development of the site.

Based in Leicester, Samuel has a broad background in tennis media. In his current role, he works closely with editors and writers to ensure coverage meets clear journalistic standards, with particular attention to verification, consistency, and timely updates when new information becomes available.

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