Magdalena Grzybowska defeated Conchita Martinez 7-5 6-2 in the Hilton Head round of 32 on clay. The upset overturned the form book — Conchita Martinez came in leading the head-to-head 1–0, defending last year's semi-final. Magdalena Grzybowska claimed a first win over Conchita Martinez in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-12 | Sopot | R16 | clay | Conchita Martinez | 6-1 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.