Jennifer Capriati defeated Lisa Raymond 6-2 6-0 in the Amelia Island quarter-final on clay. The result followed the form book — Jennifer Capriati came in leading the head-to-head 3–2. Jennifer Capriati extended the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-07-21 | Stanford | QF | hard | Jennifer Capriati | 6-1 6-7(5) 6-4 |
| 2001-02-19 | Oklahoma City | QF | carpet | Jennifer Capriati | 6-4 3-6 6-4 |
| 2001-01-07 | Sydney | R16 | hard | Lisa Raymond | 2-6 6-3 7-5 |
| 2000-06-12 | Birmingham | QF | grass | Lisa Raymond | 6-2 4-6 7-5 |
| 1999-11-01 | Quebec City | QF | hard | Jennifer Capriati | 6-4 6-2 |
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 (31 vs 46). ATP, WTA & Challenger.