Anna Kournikova defeated Steffi Graf 6-7 6-3 6-4 in the Eastbourne quarter-final on grass. The upset overturned the form book — Steffi Graf came in leading the head-to-head 2–0. Anna Kournikova claimed a first win over Steffi Graf in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Roland Garros | R16 | clay | Steffi Graf | 6-3 7-6 |
| 1996-08-26 | US Open | R16 | hard | Steffi Graf | 6-2 6-1 |