Meghann Shaughnessy defeated Jessica Steck 5-7 6-3 6-3 in the Dallas 50K round of 32 on hard. The upset overturned the form book — Jessica Steck came in leading the head-to-head 1–0. Meghann Shaughnessy claimed a first win over Jessica Steck in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-05 | Amelia Island | R64 | clay | Jessica Steck | 7-5 3-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.