Natalie Cahana defeated Maria Fernanda Landa 6-0 6-1 in the Caracas 25K qualifying round on hard. The upset overturned the form book — Maria Fernanda Landa came in leading the head-to-head 1–0. Natalie Cahana claimed a first win over Maria Fernanda Landa in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-15 | Ashkelon 25K | R32 | hard | Maria Fernanda Landa | 6-1 6-3 |