Jennifer Capriati defeated Anne Gaelle Sidot 7-5 6-7 6-3 in the Luxembourg quarter-final on hard. The upset overturned the form book — Anne Gaelle Sidot came in defending last year's round of 16, but Jennifer Capriati had been the form player, winning 3 of their last 4 on hard. Jennifer Capriati extended 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 |
| 2000-05-15 | Rome | R64 | clay | Anne Gaelle Sidot | 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.