On Sunday afternoon, the 14-seed Naomi Osaka upset top-ranked Aryna Sabalenka in the Round of 16 at the 2026 Wimbledon Championships. It was Sabalenka's earliest exit from a Grand Slam since 2022, and it adds extra pressure to her upcoming hard-court campaign.As for Osaka, it is her biggest victory since maternity leave in 2023. Since then, the Japanese superstar has had to overcome injuries and a revolving door of coaches. However, she is in great shape now and seems to have a strong coaching partnership with Tomasz Wiktorowski.Osaka has made multiple finals over the past few years, but keeps falling just short of winning a WTA tour-level title (outside of the 2025 125K e L'Open 35 de Saint-Malo). Can Osaka break through at the All England Club? It will not be easy, as she faces three tricky rounds ahead of her.QuarterfinalsKaorlina Muchova at Wimbledon. | IMAGO / SchreyerOsaka will face the 10-seed Karolina Muchova in the quarterfinal on Tuesday, July 7. Just before Wimbledon, Muchova defeated Osaka in the Bad Homburg Open final. Osaka had to retire from the match due to a minor injury. Before that, Muchova also played in the Berlin Open. She was one of the few WTA stars to play two warm-up tournaments before Wimbledon. Osaka and Muchova are 3-3 in head-to-head meetings. Historically, Muchova has fared much better on grass than Osaka. She has reached the Wimbledon quarterfinals three times, and hopes to make her first-ever semifinal appearance this week.SemifinalsJessica Pegula defeated Iva Jovic in the Wimbledon quarterfinal. | IMAGO / ISI PhotosIf Osaka makes it to the semifinals, she could face either 4-seed Jessica Pegula, 7-seed Coco Gauff, or 11-seed Belinda Bencic. Osaka is 1-1 against Pegula, 3-3 against Gauff, and 2-4 against Belinda Bencic.Pegula has just made her second Wimbledon quarterfinal appearance, with Osaka making her first. Meanwhile, Bencic reached the semifinals last year.FinalsMarta Kostyuk at Wimbledon. | IMAGO / ISI PhotosIf Osaka makes it to the final, she could face either 9-seed Linda Noskova, 12-seed Marta Kosyuk, 13-seed Jasmine Paolini, 21-seed Marie Bouzkova, 25-seed Elise Mertens, 26-seed Madison Keys, 29-seed Alex Eala, or qualifier Ashlyn Krueger.Osaka is 0-1 against Noskova, 2-0 against Kostyuk, 0-1 against Paolini, 3-0 against Bouskova, 5-3 against Mertens, 1-3 against Keys, 0-1 against Krueger, and has never faced Eala.Osaka's 2026 SeasonNaomi Osaka at Wimbledon. | IMAGO / BSR AgencyOsaka is currently the WTA World No. 14 with a singles record of 20-7 with zero titles. The four-time Grand Slam champion has not won a WTA tour-level tournament since the 2021 Australian Open. However, she is three matches away from making history.The 2026 Wimbledon Championships run through July 12. Stay locked into Sports Illustrated's Serve On SI for all of your tennis news from the court and beyond.Add us as a preferred source on GoogleFollow