Angelika Roesch defeated Melissa Middleton 6-2 6-2 in the Mogi Das Cruzes 25K round of 16 on clay. The upset overturned the form book — Melissa Middleton came in leading the head-to-head 1–0. Angelika Roesch claimed a first win over Melissa Middleton in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Grado 25K | R32 | clay | Melissa Middleton | 6-2 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.