Level, 2 wins each over 4 singles meetings since 2021. Last meeting on 31/08/2025 at U.S. Open - New York.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 31/08/2025 | U.S. Open - New York | Round 4 | hard | Osaka | 6-3 6-2 |
| 01/10/2024 | China Open - Beijing | Round 4 | hard | Gauff | 6-3 4-5 |
| 03/08/2022 | Mubadala Silicon Valley Classic - San Jose | Round 2 | hard | Gauff | 6-4 6-4 |
| 18/08/2021 | Western & Southern Open - Cincinnati | Round 2 | hard | Osaka | 6-4 3-6 4-6 |
| hard | Osaka 2 - 2 Gauff |
| 2025 | Osaka 1 - 0 Gauff |
| 2024 | Osaka 0 - 1 Gauff |
| 2022 | Osaka 0 - 1 Gauff |
| 2021 | Osaka 1 - 0 Gauff |
116 wins, 64 losses since 2021 (64.4%).
Last matches: D V V D V
270 wins, 97 losses since 2021 (73.6%).
Last matches: D V V D V
Level, 2 wins each over 4 singles meetings since 2021.
On 31/08/2025, at U.S. Open - New York (Round 4): Naomi Osaka won 6-3 6-2.