Chanda Rubin defeated Elena Pampoulova 6-4 6-1 in the Key Biscayne round of 64 on hard. The result followed the form book — Chanda Rubin came in leading the head-to-head 1–0, defending last year's round of 64. Chanda Rubin extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-18 | Australian Open | R64 | hard | Chanda Rubin | 4-6 7-6(4) 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.