Naomi Osaka of Japan reacts after defeating Daria Kasatkina of...

Naomi Osaka of Japan reacts after defeating Daria Kasatkina of Australia in a third-round match on Saturday at the U.S. Open in Queens. Credit: Getty Images/Maddie Meyer

It has been six years since Coco Gauff and Naomi Osaka last played at the U.S. Open, but that third-round meeting in 2019 remains one of the most memorable matches for both players.

Gauff was a skinny, exuberant 15-year-old making her U.S. Open debut. Osaka was the 21-year-old defending U.S. Open champion and the second-highest paid female athlete in the world. After taking little more than an hour to wipe the court with Gauff in straight sets, Osaka put in some extra time helping her young opponent wipe away her tears.

Much has changed since that emotional meeting in 2019. Gauff, the tournament’s No. 3 seed, has ascended to become one of the top players in the game while Osaka, who skipped the entire 2023 season for maternity leave, is slowly working her way back to relevance.

This time it is Osaka, not Gauff, who stands to gain the most when the two former U.S. Open champions meet Monday in the round of 16 for a match that will most certainly be played, like their last match here was, in front of a packed crowd in Arthur Ashe Stadium.

While Gauff will be competing in the fourth round of the U.S. Open for the fourth consecutive year, this marks the first time that Osaka, currently ranked 24th, has gotten this far in a Grand Slam tournament since 2021 when she won the Australian Open. Osaka knows the moment is special.

“I think it’s more like for me the journey getting back here,” said Osaka, who advanced by defeating No. 15 Daria Kasatkina 6-0, 4-6, 6-3 Saturday. “We obviously had like a really special moment here that a lot of people remember. For me, she’s like the main star of the U.S. Open. I haven’t played on Ashe yet. So, it’s just a combination of those things.”

Gauff, who advanced by beating No. 28 Magdalena Frech of Poland 6-3, 6-1 Saturday, was asked about facing Osaka before Osaka’s third round match was over.

“It would be kind of a déjà vu situation but hopefully it will be with a different result.” Gauff said.

This will mark the sixth time the two players have met one another. Gauff has won three of the previous five matches, but the record is a little deceptive. Osaka’s two wins came when Gauff was 15 at the U.S. Open and 17 in Cincinnati. Gauff’s most famous win over Osaka came when she was 15 and beat her at the third round of the Australian Open in 2020. She also won their last two matches, beating her three years ago in San Jose in straight sets and last year in Beijing when Osaka retired with a back injury after the two split sets.

There is a case to be made for Osaka, a four-time Grand Slam champion, pulling off an upset.  She has been quietly working her way back into form. At the Canadian Open in August, Osaka beat four higher ranked opponents on the way to runner-up finish. As result, her ranking jumped from 49 to 26 with the result being that she would be seeded for the first time in a Grand Slam tournament since 2022 at the Australian Open, which she won.

Gauff, by contrast, has had some struggles since winning her second Grand Slam tournament at the French Open this year. Days before the start of this year’s U.S. Open, Gauff shook up her coaching staff, replacing coach Matt Daly with Gavin MacMillan, a biomechanics expert whom she is hoping can fix her unreliable second serve.

Changing something as fundamental as her serve has proved to be frustrating early on. Gauff could be seen crying into a towel during her second-round match against Croatian Donna Vekic. Though she recovered to win the match in straight sets, she double faulted seven times in the opening set and was broken in four of her service games.

Her win Saturday, however, was the best of the tournament as she had only four double faults against Frech, putting her opponent away in one hour and 13 minutes in front of a rabid U.S. Open crowd.

Gauff is the most popular player at the tournament, while Osaka, who was raised in the United States but is a Japanese citizen, would be a fan favorite in a match against almost any other opponent. This was not something lost on Osaka.

“Can someone come to the match and cheer for me, because it’s kind of tough playing an American here so I hope you guys have adopted me as well?” Osaka said when asked about facing Gauff. “I kind of also see her as a little sister, so it’s really cool to be playing her here again.”

Cool match, hot ticket.

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