Jennifer Capriati defeated Anna Kournikova 7-6 6-4 in the Zurich quarter-final on hard. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 3–0, but Jennifer Capriati had been the form player, winning 6 of their last 8 on hard. Jennifer Capriati claimed a first win over Anna Kournikova in four meetings, narrowing 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 |
| 2000-01-07 | Sydney | R16 | hard | Anna Kournikova | 6-4 7-5 |
| 1999-04-05 | Amelia Island | R32 | clay | Anna Kournikova | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.