Natalia Zvereva defeated Jana Novotna 6-4 6-4 in the Philadelphia round of 16 on carpet. The upset overturned the form book — Jana Novotna came in leading the head-to-head 4–0, defending last year's quarter-final. Natalia Zvereva claimed a first win over Jana Novotna in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-02 | Tokyo | QF | hard | Jana Novotna | 7-5 |
| 1998-06-15 | Eastbourne | SF | grass | Jana Novotna | 6-2 6-1 |
| 1997-06-17 | Eastbourne | SF | grass | Jana Novotna | 6-7 6-0 7-5 |
| 1993-05-24 | Roland Garros | R16 | clay | Jana Novotna | 6-3 6-3 |