Conchita Martinez defeated Naoko Sawamatsu 6-2 6-2 in the Key Biscayne round of 32 on hard. The upset overturned the form book — Naoko Sawamatsu came in defending last year's round of 64, but Conchita Martinez had been the form player, winning 3 of their last 7 on hard. Conchita Martinez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-09-15 | Tokyo | QF | hard | Naoko Sawamatsu | 7-6 6-4 |
| 1995-08-28 | US Open | R32 | hard | Conchita Martinez | 6-1 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.