Jennifer Brady defeated Jelena Ostapenko 7-6 0-6 7-6 in the Montreal round of 64 on hard. Jennifer Brady extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2023-08-07 | Montreal | R64 | hard | Jennifer Brady | 7-6 0-6 7-6 |
| 2021-08-18 | Cincinnati | R32 | hard | Jelena Ostapenko | 6-7(2) 5-4 |
| 2021-08-16 | Cincinnati | R32 | hard | Jelena Ostapenko | 6-7 5-4 |
| 2021-04-29 | Madrid | R32 | clay | Jennifer Brady | 6-2 6-1 |
| 2019-02-18 | Dubai | R64 | hard | Jennifer Brady | 6-4 6-0 |
Averages over each player's completed matches in the selected window (16 vs 164). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). 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