Esme De Villiers defeated Lara Van Rooyen 6-3 6-2 in the Lexington 25K round of 16 on hard. The upset overturned the form book — Lara Van Rooyen came in leading the head-to-head 1–0. Esme De Villiers claimed a first win over Lara Van Rooyen in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-11-25 | Durban 5K | SF | hard | Lara Van Rooyen | 7-6 4-6 6-0 |