Anna Kalinskaya leads 3 to 0 over 3 singles meetings since 2023. Last meeting on 16/02/2026 at Dubai Duty Free Championships - Dubai.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 16/02/2026 | Dubai Duty Free Championships - Dubai | Round 1 | hard | Kalinskaya | 6-2 1-6 4-6 |
| 24/03/2024 | Miami Open - Miami | Round 3 | hard | Kalinskaya | 6-3 6-1 |
| 09/01/2023 | Adelaide International 2 - Adelaide | Round 1 | hard | Kalinskaya | 3-6 4-6 |
| hard | Ostapenko 0 - 3 Kalinskaya |
| 2026 | Ostapenko 0 - 1 Kalinskaya |
| 2024 | Ostapenko 0 - 1 Kalinskaya |
| 2023 | Ostapenko 0 - 1 Kalinskaya |
161 wins, 112 losses since 2021 (59.0%).
Last matches: D D D D V
160 wins, 116 losses since 2021 (58.0%).
Last matches: V D V D V
Anna Kalinskaya leads 3 to 0 over 3 singles meetings since 2023.
On 16/02/2026, at Dubai Duty Free Championships - Dubai (Round 1): Anna Kalinskaya won 6-2 1-6 4-6.