Alexandra Stevenson defeated Anke Huber 7-5 2-6 6-1 in the Philadelphia round of 32 on carpet. The upset overturned the form book — Anke Huber came in leading the head-to-head 1–0, defending last year's round of 32. Alexandra Stevenson claimed a first win over Anke Huber in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-09 | Manhattan Beach | R32 | hard | Anke Huber | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.