Ann Grossman defeated Conchita Martinez 6-3 2-6 6-4 in the US Open round of 128 on hard. The upset overturned the form book — Conchita Martinez came in leading the head-to-head 2–0, defending last year's quarter-final. Ann Grossman claimed a first win over Conchita Martinez in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-05-27 | Roland Garros | R32 | clay | Conchita Martinez | 6-2 6-1 |
| 1992-05-25 | Roland Garros | R32 | clay | Conchita Martinez | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.