Anna Kournikova defeated Jennifer Capriati 6-4 7-5 in the Sydney round of 16 on hard. The result followed the form book — Anna Kournikova came in leading the head-to-head 2–1, defending last year's round of 16. Anna Kournikova extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-13 | WTA Tour Championships | R16 | carpet | Anna Kournikova | 6-4 6-4 |
| 2000-10-09 | Zurich | QF | hard | Jennifer Capriati | 7-6(4) 6-4 |
| 1999-04-05 | Amelia Island | R32 | clay | Anna Kournikova | 6-3 6-3 |
Averages from each player's recent completed matches. ATP, WTA & Challenger.