Nicole Pratt defeated Anna Kournikova 6-7 6-1 6-3 in the San Diego round of 32 on hard. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 3–0, defending last year's semi-final. Nicole Pratt claimed a first win over Anna Kournikova in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-04 | Philadelphia | R16 | carpet | Anna Kournikova | 6-0 6-2 |
| 2000-04-10 | Amelia Island | R16 | clay | Anna Kournikova | 6-0 7-5 |
| 2000-01-31 | Tokyo | R16 | hard | Anna Kournikova | 6-2 1-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.