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CINCINNATI—Naomi Osaka’s no good, very bad week in the Midwest began before she even arrived in Mason for the Cincinnati Open.

“lol @united lost my bags and if I don’t get them tonight or tomorrow I literally can’t play Cincinnati 😂😂😂” the former No. 1 informed fans on social media on Friday.

Oksaka was flying in from the National Bank Open in Toronto, where she had just endured a thudding loss to Elise Mertens. It was the second time she had lost to the tenacious Belgian since coming back from maternity leave at the start of 2024, but the four-time Grand Slam champion was already looking ahead to her next outing scheduled for the following week.

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“I'm playing Cincy, and then I guess there's no other tournament [before the US Open],” she insisted in her post-match press conference.

The only problem? Osaka wasn’t in the main draw, her ranking of No. 95 still too low to automatically appear at 1000-level tournaments.

Questions of whether the Japanese star would receive a wild card were answered over the weekend when it was revealed that Osaka would play main-draw qualifying for the first time since February 2018.

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Playing on a full Grandstand court, fans were treated to a rare up-close look at Osaka as she battled past Anna Blinkova, 6-2, 2-6, 6-2. The victory over the No. 11 seed put her one win away from the main draw, she was unable to secure her spot on Monday, losing to American Ashlyn Krueger, 6-3, 2-6, 6-3.

Osaka led Krueger 3-1 in the final set only to lose the final five games on Center Court.

The two-time US Open champion has made Flushing Meadows the cornerstone of her comeback, repeatedly citing the summer swing as the time where she hopes to peak.

Osaka last won the US Open in 2020, defeating Victoria Azarenka in three dramatic sets in front of an empty Arthur Ashe Stadium due to the ongoing COVID-19 pandemic.

Osaka last won the US Open in 2020, defeating Victoria Azarenka in three dramatic sets in front of an empty Arthur Ashe Stadium due to the ongoing COVID-19 pandemic.

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“I'm kind of setting myself up for September anyway,” she said after losing a heartbreaking Roland Garros second round to Iga Swiatek.

Osaka has also come to New York undercooked in years past, none more famously than in 2018, when she first opened up about feeling depressed after disappointing results in Canada and Cincinnati.

“If anyone was following Cincy you would know my match I lost but I feel like it was a step in the right direction, things weren't working the way I wanted but I finally felt that fun feeling playing tennis,” Osaka wrote at the time.

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She would win her first Grand Slam tournament less than a month later. Her last US Open victory came in 2020, during the "COVID" Open played without spectators, and her most recent major win was Down Under at the 2021 Australian Open.

Osaka posted reflections on her current state of mind to Instagram on Tuesday:

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"In a weird way I've come to appreciate losses, you don't play tennis for 20+ years without your fair share of them," she wrote. "You learn from a loss and then eagerly await your next opportunity to put what you learned to test.

"My biggest issue currently isn't losses though, my biggest issue is that I don't feel like I'm in my body. It's a strange feeling, missing balls I shouldn't miss, hitting balls softer than I remember I used to. I try and tell myself 'it's fine you're doing great, just get through this one and keep pushing,' mentally it's really draining though. Internally I hear myself screaming 'what the hell is happening?!?!'"

Osaka will need a wild card to enter the main draw of the 2024 US Open—having exhausted the limit of Grand Slam tournaments she can enter with the protected ranking from maternity leave—or she will be forced to play qualifying again.

But as Swiatek can attest, Osaka remains the most dangerous floater currently competing in the women’s game, and the “US Open or bust” mentality may be just what the 26-year-old needs to shift into turbo in time for the end of the season.