Nathalie Dechy defeated Anna Kournikova 7-5 5-7 7-6 in the Indian Wells round of 32 on hard. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 1–0, defending last year's round of 64. Nathalie Dechy claimed a first win over Anna Kournikova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Eastbourne | QF | grass | Anna Kournikova | 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.