Anna Kournikova defeated Anke Huber 3-6 6-4 6-4 in the Wimbledon round of 32 on grass. The upset overturned the form book — Anke Huber came in leading the head-to-head 3–2. Anna Kournikova narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-02 | Tokyo | R32 | hard | Anna Kournikova | 7-6 6-0 |
| 1998-02-18 | Hanover | QF | carpet | Anna Kournikova | 6-4 3-6 6-4 |
| 1998-02-09 | Paris | R16 | carpet | Anke Huber | 6-2 1-6 6-4 |
| 1997-08-04 | Manhattan Beach | R32 | hard | Anke Huber | 6-0 6-1 |
| 1997-03-07 | Indian Wells | R32 | hard | Anke Huber | 3-6 6-2 6-2 |