Meghann Shaughnessy defeated Florencia Labat 6-7 6-1 7-6 in the Auckland round of 32 on hard. The upset overturned the form book — Florencia Labat came in leading the head-to-head 1–0, defending last year's round of 16. Meghann Shaughnessy claimed a first win over Florencia Labat in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-11 | Largo 50K | R32 | hard | Florencia Labat | 3-6 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.