

Madison Keys defeated Jelena Ostapenko 7-5 6-2 in the Charleston round of 16 on clay. The result followed the form book — Madison Keys came in ranked #23, leading the head-to-head 3–2, defending last year's semi-final. Madison Keys extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-01-06 | Adelaide | R16 | hard | Madison Keys | 3-6 6-4 6-3 |
| 2023-02-13 | Doha | R32 | hard | Jelena Ostapenko | 7-5 6-2 |
| 2022-08-15 | Cincinnati | R32 | hard | Madison Keys | 6-4 7-5 |
| 2022-06-20 | Eastbourne | R16 | grass | Jelena Ostapenko | 6-3 RET |
| 2016-06-13 | Birmingham | QF | grass | Madison Keys | 6-7(1) 6-4 6-2 |
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 (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Keys M.: 7 days rest · 1 match, 23 games (7d) · Ostapenko J.: 10 days rest · 3 matches (14d). Higher means fresher. About