Level, 1 wins each over 2 singles meetings since 2025. Last meeting on 27/10/2026 at Toray Pan Pacific Open - Tokyo.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 27/10/2026 | Toray Pan Pacific Open - Tokyo | Round 1 | hard | Osaka | 6-3 7-6(4) |
| 24/03/2025 | Miami Open - Miami | Round 4 | hard | Paolini | 3-6 6-4 6-4 |
| hard | Osaka 1 - 1 Paolini |
| 2026 | Osaka 1 - 0 Paolini |
| 2025 | Osaka 0 - 1 Paolini |
117 wins, 65 losses since 2021 (64.3%).
Last matches: D V D V V
211 wins, 135 losses since 2021 (61.0%).
Last matches: D D V D V
Level, 1 wins each over 2 singles meetings since 2025.
On 27/10/2026, at Toray Pan Pacific Open - Tokyo (Round 1): Naomi Osaka won 6-3 7-6(4).