Natalia Zvereva defeated Andrea Glass 6-4 3-6 6-0 in the Key Biscayne round of 64 on hard. The result followed the form book — Natalia Zvereva came in leading the head-to-head 1–0, defending last year's round of 32. Natalia Zvereva extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | Berlin | R64 | grass | Natalia Zvereva | 3-6 6-2 6-3 |