Pavlina Nola defeated Florencia Labat 6-1 2-6 6-0 in the Largo 50K round of 16 on hard. The upset overturned the form book — Florencia Labat came in leading the head-to-head 1–0. Pavlina Nola claimed a first win over Florencia Labat in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Nashville 25K | QF | hard | Florencia Labat | 6-2 6-2 |