Jessica Steck defeated Meghann Shaughnessy 7-5 3-6 6-1 in the Amelia Island round of 64 on clay. The upset overturned the form book — Meghann Shaughnessy came in leading the head-to-head 1–0. Jessica Steck claimed a first win over Meghann Shaughnessy in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Dallas 50K | R32 | hard | Meghann Shaughnessy | 5-7 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.