Steffi Graf defeated Anna Kournikova 6-2 6-1 in the US Open round of 16 on hard. The result followed the form book — Steffi Graf came in defending the title. Steffi Graf extended 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 |
| 1998-06-15 | Eastbourne | QF | grass | Anna Kournikova | 6-7 6-3 6-4 |