Lilia Osterloh defeated Anna Kournikova 6-1 6-4 in the Indian Wells round of 128 on hard. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 1–0, but Lilia Osterloh had been the form player, winning 3 of their last 7 on hard. Lilia Osterloh claimed a first win over Anna Kournikova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-05-13 | Rome | R32 | clay | Anna Kournikova | 6-1 4-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.