Lilia Osterloh defeated Samantha Reeves 6-1 6-0 in the Amelia Island q32 on clay. The upset overturned the form book — Samantha Reeves came in leading the head-to-head 4–2, defending last year's round of 64. Lilia Osterloh narrowed the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-11-03 | Pittsburgh PA 50K | R32 | hard | Lilia Osterloh | 6-3 4-6 6-0 |
| 2003-02-03 | Midland 75K | R32 | hard | Samantha Reeves | 6-3 6-2 |
| 2002-09-10 | Waikoloa | R32 | hard | Samantha Reeves | 6-1 6-2 |
| 2002-01-06 | Canberra | R16 | hard | Lilia Osterloh | 3-6 6-4 6-2 |
| 2001-11-05 | Pittsburgh 50K | QF | hard | Samantha Reeves | 6-4 1-6 6-4 |
| 1999-08-30 | US Open | R128 | hard | Samantha Reeves | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.