Anna Smashnova defeated Jana Novotna 6-4 6-2 in the Roland Garros round of 128 on clay. The upset overturned the form book — Jana Novotna came in leading the head-to-head 1–0, defending last year's quarter-final. Anna Smashnova claimed a first win over Jana Novotna in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-18 | Key Biscayne | R64 | hard | Jana Novotna | 6-0 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.