Natalia Zvereva defeated Kimberly Po Messerli 7-6 2-6 6-1 in the San Diego round of 32 on hard. The result followed the form book — Natalia Zvereva came in leading the head-to-head 1–0. Natalia Zvereva extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R128 | grass | Natalia Zvereva | 5-7 6-1 6-3 |