Ai Sugiyama defeated Brie Rippner 6-3 7-5 in the Miami round of 64 on hard. The result followed the form book — Ai Sugiyama came in leading the head-to-head 1–0, defending last year's round of 64. Ai Sugiyama extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-03 | Hope Island | QF | hard | Ai Sugiyama | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.