

Jelena Ostapenko advanced when Madison Keys retired 6-3 in the Eastbourne round of 16. Jelena Ostapenko narrowed 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 |
| 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
Ostapenko J.: 5 days rest · 1 match, 16 games (7d) · Keys M.: 1 day rest · 3 matches, 67 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