Level, 2 wins each over 4 singles meetings since 2024. Last meeting on 30/07/2025 at Omnium Banque Nationale - Montreal.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 30/07/2025 | Omnium Banque Nationale - Montreal | Round 2 | hard | Osaka | 6-4 6-7(6) 3-6 |
| 16/06/2025 | Berlin Ladies Open - Berlin | Round 1 | grass | Samsonova | 6-3 6-7(3) 4-5 |
| 20/03/2025 | Miami Open - Miami | Round 2 | hard | Osaka | 6-2 6-4 |
| 25/04/2024 | Mutua Madrid Open - Madrid | Round 2 | clay | Samsonova | 2-6 6-4 5-7 |
| hard | Osaka 2 - 0 Samsonova |
| grass | Osaka 0 - 1 Samsonova |
| clay | Osaka 0 - 1 Samsonova |
| 2025 | Osaka 2 - 1 Samsonova |
| 2024 | Osaka 0 - 1 Samsonova |
113 wins, 62 losses since 2021 (64.6%).
Last matches: V V D V V
170 wins, 124 losses since 2021 (57.8%).
Last matches: D D V D V
Level, 2 wins each over 4 singles meetings since 2024.
On 30/07/2025, at Omnium Banque Nationale - Montreal (Round 2): Naomi Osaka won 6-4 6-7(6) 3-6.