Jennifer Hopkins defeated Vanessa Webb 4-6 6-3 6-2 in the Hilton Head 10K semi-final on hard. The upset overturned the form book — Vanessa Webb came in leading the head-to-head 1–0. Jennifer Hopkins claimed a first win over Vanessa Webb in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Mount Pleasant 25K | F | hard | Vanessa Webb | 6-2 5-7 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.