

Anna Kalinskaya defeated Madison Keys 6-2 6-4 in the Charleston round of 16 on clay. The upset overturned the form book — Madison Keys came in leading the head-to-head 2–0, defending last year's round of 32. Anna Kalinskaya claimed a first win over Madison Keys in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-04-22 | Madrid | R32 | clay | Madison Keys | 7-5 7-6 |
| 2022-05-23 | Roland Garros | R128 | clay | Madison Keys | 6-3 3-6 6-4 |
Averages over each player's completed matches in the selected window (76 vs 81). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Kalinskaya A.: 7 days rest · 1 match, 25 games (7d) · Keys M.: 3 days rest · 3 matches, 71 games (7d). Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Per-surface Serve / Return Rating (0–100, percentile within the clay field, opponent-adjusted over 52 weeks). About