Anna Kournikova defeated Lilia Osterloh 6-1 4-6 6-1 in the Rome round of 32 on clay. The upset overturned the form book — Lilia Osterloh came in leading the head-to-head 1–0, defending last year's round of 32. Anna Kournikova claimed a first win over Lilia Osterloh in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-03-06 | Indian Wells | R128 | hard | Lilia Osterloh | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.