Serena Williams defeated Anna Kournikova 6-2 4-6 6-3 in the Sydney round of 16 on hard. The result followed the form book — Serena Williams came in leading the head-to-head 1–0, defending last year's quarter-final. Serena Williams extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-14 | Montreal | R16 | hard | Serena Williams | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.