Cara Black defeated Jennifer Capriati 5-7 6-1 6-2 in the Indian Wells round of 64 on hard. The upset overturned the form book — Jennifer Capriati came in leading the head-to-head 1–0. Cara Black claimed a first win over Jennifer Capriati in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | Strasbourg | R16 | clay | Jennifer Capriati | 7-6 6-4 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (15 vs 31). ATP, WTA & Challenger.