Angela Haynes defeated Lilia Osterloh 7-5 6-2 in the Ponte Vedra Beach q16 on clay. The upset overturned the form book — Lilia Osterloh came in leading the head-to-head 2–1. Angela Haynes narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-04-26 | Charlottesville VA 50K | R32 | clay | Lilia Osterloh | 6-3 6-4 |
| 2006-08-22 | US Open | Q128 | hard | Angela Haynes | 4-6 6-3 6-2 |
| 2006-04-17 | Dothan AL 75K | R32 | clay | Lilia Osterloh | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.