By surface
| Surface | Madison Keys | Anna Kalinskaya |
|---|---|---|
| Clay | 2 | 1 |
All meetings (3)
| Date | Tour | Tournament | Round | Surface | Winner | Set 1 | Set 2 | Set 3 | Set 4 | Set 5 |
|---|---|---|---|---|---|---|---|---|---|---|
| 2025-04-22 | WTA | Madrid | Round of 32 | Clay | Madison Keys | 7-5 | 7-63 | |||
| 2025-03-31 | WTA | Charleston | Round of 16 | Clay | Anna Kalinskaya | 2-6 | 4-6 | |||
| 2022-05-23 | WTA | Roland Garros | Round of 128 | Clay | Madison Keys | 6-3 | 3-6 | 6-4 |