Lilia Osterloh defeated Tracy Almeda Singian 6-3 3-6 6-1 in the Midland 75K round of 16 on hard. The upset overturned the form book — Tracy Almeda Singian came in leading the head-to-head 1–0, but Lilia Osterloh had been the form player, winning 2 of their last 7 on hard. Lilia Osterloh claimed a first win over Tracy Almeda Singian in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-04-10 | Amelia Island | R64 | clay | Tracy Almeda Singian | 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.