A. Kalinskaya leads the head-to-head 4-1 since 2018 against J. Ostapenko, over 5 matches.
| Surface | A. Kalinskaya | J. Ostapenko |
|---|---|---|
| Clay | 0 | 1 |
| Hard | 4 | 0 |
| Date | Winner | Score | Event |
|---|---|---|---|
| May 11, 2026 | J. Ostapenko | 2 - 0 | Rome · 1/8-finals · clay |
| Feb. 16, 2026 | A. Kalinskaya | 2 - 1 | WTA Dubai · 1/32-finals · hard |
| March 24, 2024 | A. Kalinskaya | 2 - 0 | WTA Miami · 1/16-finals · hard |
| Feb. 21, 2024 | A. Kalinskaya | 2 - 0 | WTA Dubai · 1/8-finals · hard |
| Jan. 10, 2023 | A. Kalinskaya | 2 - 0 | Adelaide 2 · 1/16-finals · hard |