Daniela Olivera defeated Alienor Tricerri 3-6 6-4 6-4 in the Montevideo 10K round of 16 on clay. The upset overturned the form book — Alienor Tricerri came in leading the head-to-head 1–0. Daniela Olivera claimed a first win over Alienor Tricerri in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Caracas 10K | SF | hard | Alienor Tricerri | 6-4 6-4 |