Level, 2 wins each over 4 singles meetings since 2022. Last meeting on 08/01/2025 at Adelaide International - Adelaide.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 08/01/2025 | Adelaide International - Adelaide | Round 2 | hard | Keys | 3-6 6-4 6-3 |
| 13/02/2023 | Qatar TotalEnergies Open - Doha | Round 1 | hard | Ostapenko | 7-5 6-2 |
| 18/08/2022 | Western & Southern Open - Cincinnati | Round 2 | hard | Keys | 6-4 7-5 |
| 23/06/2022 | Viking International - Eastbourne | Round 3 | grass | Ostapenko | 6-3 0-0 ret. |
| hard | Keys 2 - 1 Ostapenko |
| grass | Keys 0 - 1 Ostapenko |
| 2025 | Keys 1 - 0 Ostapenko |
| 2023 | Keys 0 - 1 Ostapenko |
| 2022 | Keys 1 - 1 Ostapenko |
165 wins, 90 losses since 2021 (64.7%).
Last matches: D V V D V
167 wins, 116 losses since 2021 (59.0%).
Last matches: D D V V V
Level, 2 wins each over 4 singles meetings since 2022.
On 08/01/2025, at Adelaide International - Adelaide (Round 2): Madison Keys won 3-6 6-4 6-3.