Vanessa Henke defeated Melissa Middleton 0-6 6-3 6-4 in the Mahwah NJ 50K round of 32 on hard. The upset overturned the form book — Melissa Middleton came in leading the head-to-head 1–0. Vanessa Henke claimed a first win over Melissa Middleton in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-05 | Darmstadt 25K | R16 | clay | Melissa Middleton | 3-6 7-6 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.