Naomi Osaka and Jasmine Paolini are set to do battle for only the second time in their careers later this week.
Osaka and Paolini, both former top five-ranked players on the WTA circuit, have been drawn to play each other in the Pan Pacific Open first round.
Paolini will be hoping to end her year on a high amid a disappointing campaign thus far, while Osaka will look to build upon what has been a strong season for the Japanese four-time major champion.
| Result | Year | Tournament | Surface | Opponent | Score |
| Win | 2018 | US Open | Hard | Serena Williams | 6ā2, 6ā4 |
| Win | 2019 | Australian Open | Hard | Petra Kvitova | 7ā6(7ā2), 5ā7, 6ā4 |
| Win | 2020 | US Open | Hard | Victoria Azarenka | 1ā6, 6ā3, 6ā3 |
| Win | 2021 | Australian Open | Hard | Jennifer Brady | 6ā4, 6ā3 |
The duo last met at the 2025 Miami Open; on that occasion, Osaka let the match slip through her grasp.
Naomi Osaka cannot afford to be wasteful on break points against Jasmine Paolini
Naomi Osaka had trouble converting break-point opportunities when she last competed against Jasmine Paolini at the 2025 Miami Open.
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The result on the day could have been very different, had Osaka managed to convert more than three of her 15 break point chances.
The Japanese star failed to do so and ultimately paid the price for her wastefulness.
Paolini, on the other hand, was efficient in taking advantage of her opportunities, converting three of her five break-points opportunities on the Osaka serve.
The Italianās ruthlessness spurred her on to a 3-6, 6-4, 6-4 victory in Florida.
When will Naomi Osaka and Jasmine Paolini play each other in Tokyo?
Osaka and Paolini still have a significant amount of time to prepare ahead of the first-round contest in Japan.
The duo are set to take to the court on Tuesday at 10:30am local time.
The winner of their contest will play either Tereza Valentova or Mia Pohankova in the second round.
Should Osaka or Paolini advance further, they will likely face second seed and Wuhan Open champion Maja Chwalinska in the third round.
Chwalinska, the Roland Garros finalist, confirmed her participation in the Pan Pacific Open earlier this week.
Chwalinska entered the event shortly after withdrawing from the Ningbo Open through injury.
