A. Kalinskaya and C. Osorio are level 2-2 in their head-to-head since 2018 over 4 matches.
| Surface | A. Kalinskaya | C. Osorio |
|---|---|---|
| Clay | 1 | 0 |
| Hard | 1 | 1 |
| Grass | 0 | 1 |
| Date | Winner | Score | Event |
|---|---|---|---|
| May 30, 2026 | A. Kalinskaya | 2 - 1 | French Open · 1/16-finals · clay |
| Sept. 27, 2025 | C. Osorio | 2 - 1 | Beijing · 1/32-finals · hard |
| Feb. 25, 2022 | A. Kalinskaya | 2 - 0 | Guadalajara · Quarter-finals · hard |
| June 28, 2021 | C. Osorio | 2 - 1 | Wimbledon · 1/64-finals · grass |