Natalia Zvereva defeated Kimberly Po Messerli 6-1 3-6 6-2 in the US Open round of 32 on hard. The result followed the form book — Natalia Zvereva came in leading the head-to-head 2–0, defending last year's round of 128. Natalia Zvereva extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | R128 | grass | Natalia Zvereva | 5-7 6-1 6-3 |
| 1997-07-28 | San Diego | R32 | hard | Natalia Zvereva | 7-6 2-6 6-1 |