Lilia Osterloh defeated Mary Pierce 6-7 6-4 6-4 in the Tokyo round of 16 on hard. The upset overturned the form book — Mary Pierce came in leading the head-to-head 1–0. Lilia Osterloh claimed a first win over Mary Pierce in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-18 | Key Biscayne | R64 | hard | Mary Pierce | 6-1 6-1 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (52 vs 61). ATP, WTA & Challenger.