Lisa Raymond defeated Lilia Osterloh 2-6 6-2 6-2 in the Waikoloa quarter-final on hard. The result followed the form book — Lisa Raymond came in leading the head-to-head 2–1. Lisa Raymond extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-08-08 | Los Angeles | R64 | hard | Lisa Raymond | 6-0 6-2 |
| 2001-01-29 | Tokyo | R32 | hard | Lisa Raymond | 6-1 6-4 |
| 1999-02-22 | Oklahoma | R32 | hard | Lilia Osterloh | 2-6 6-2 6-2 |
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 (46 vs 52). ATP, WTA & Challenger.