

Madison Keys defeated Jelena Ostapenko 6-4 7-5 in the Cincinnati round of 32 on hard. The result followed the form book — Madison Keys came in ranked #24, leading the head-to-head 3–2, defending last year's round of 64. 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 |
| 2022-06-20 | Eastbourne | R16 | grass | Jelena Ostapenko | 6-3 |
| 2019-04-01 | Charleston | R16 | clay | Madison Keys | 7-5 6-2 |
| 2016-06-13 | Birmingham | QF | grass | Madison Keys | 6-7 6-4 6-2 |
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.: 2 days rest · 1 match, 28 games (7d) · Ostapenko J.: 3 days rest · 1 match, 16 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 hard field, opponent-adjusted over 52 weeks). About