Steffi Graf defeated Anna Kournikova 6-3 7-6 in the Roland Garros round of 16 on clay. The upset overturned the form book — Anna Kournikova came in defending last year's round of 16. Steffi Graf extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-06-15 | Eastbourne | QF | grass | Anna Kournikova | 6-7 6-3 6-4 |
| 1996-08-26 | US Open | R16 | hard | Steffi Graf | 6-2 6-1 |