Esme De Villiers defeated Antonella Serra Zanetti 1-6 6-0 7-6 in the Sao Paulo 25K round of 32 on clay. The upset overturned the form book — Antonella Serra Zanetti came in leading the head-to-head 1–0. Esme De Villiers claimed a first win over Antonella Serra Zanetti in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Nashville 25K | R32 | hard | Antonella Serra Zanetti | 1-6 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.