Anne Gaelle Sidot defeated Anna Kournikova 6-3 6-4 in the Wimbledon round of 64 on grass. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 2–0, defending last year's round of 16. Anne Gaelle Sidot claimed a first win over Anna Kournikova in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-01-29 | Tokyo | QF | hard | Anna Kournikova | 7-6(4) 6-2 |
| 2000-01-31 | Tokyo | R32 | hard | Anna Kournikova | 6-3 6-2 |