Anne Gaelle Sidot defeated Jennifer Capriati 6-3 7-5 in the Rome round of 64 on clay. The upset overturned the form book — Jennifer Capriati came in leading the head-to-head 2–0. Anne Gaelle Sidot claimed a first win over Jennifer Capriati in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-09 | Zurich | R16 | hard | Jennifer Capriati | 6-3 6-1 |
| 2000-09-23 | Luxembourg | QF | hard | Jennifer Capriati | 7-5 6-7(6) 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.