

Daria Kasatkina defeated Madison Keys 6-7 6-4 6-2 in the Charleston quarter-final on clay. The upset overturned the form book — Madison Keys came in ranked #22, leading the head-to-head 10–1, defending last year's round of 16. Daria Kasatkina narrowed the head-to-head to 10–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-01-06 | Adelaide | QF | hard | Madison Keys | 6-1 6-3 |
| 2023-06-26 | Eastbourne | F | grass | Madison Keys | 6-2 7-6(13) |
| 2022-10-10 | San Diego | R16 | hard | Madison Keys | 6-4 6-3 |
| 2022-01-03 | Melbourne 2 | R16 | hard | Daria Kasatkina | 7-6(4) 2-6 6-3 |
| 2020-01-20 | Australian Open | R128 | hard | Madison Keys | 6-3 6-1 |
| 2019-09-16 | Osaka | R32 | hard | Madison Keys | 6-3 6-4 |
| 2019-08-12 | Cincinnati | R32 | hard | Madison Keys | 6-4 6-1 |
| 2018-10-29 | Zhuhai | R16 | hard | Madison Keys | 6-2 6-4 |
| 2017-08-14 | Cincinnati | R32 | hard | Madison Keys | 6-2 6-1 |
| 2016-09-26 | Wuhan | R16 | hard | Madison Keys | 6-1 4-6 6-4 |
| 2016-08-08 | Olympics | QF | hard | Madison Keys | 6-3 6-1 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (184 vs 153). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
The Umpiry Score combines match-context factors — matchup, form, fatigue, travel and motivation — into a single 0–10 score, updated daily. Read how it works.
Kasatkina D.: 9 days rest · 3 matches (14d) · Keys M.: 6 days rest · 1 match, 23 games (7d). Higher means fresher. About