Vanessa Webb defeated Jennifer Hopkins 6-2 5-7 6-3 in the Mount Pleasant 25K final on hard. The upset overturned the form book — Jennifer Hopkins came in leading the head-to-head 1–0. Vanessa Webb claimed a first win over Jennifer Hopkins in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-07 | Hilton Head 10K | SF | hard | Jennifer Hopkins | 4-6 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.