Mary Joe Fernandez defeated Lisa Raymond 6-7 6-2 6-2 in the Roland Garros round of 16 on clay. Mary Joe Fernandez extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | Berlin | R32 | grass | Lisa Raymond | 3-6 6-1 6-0 |
| 1998-09-21 | Tokyo | R32 | hard | Mary Joe Fernandez | 7-6 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.