Alienor Tricerri defeated Daniela Olivera 6-4 6-4 in the Caracas 10K semi-final on hard. The upset overturned the form book — Daniela Olivera came in leading the head-to-head 1–0. Alienor Tricerri claimed a first win over Daniela Olivera in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Montevideo 10K | R16 | clay | Daniela Olivera | 3-6 6-4 6-4 |