Jill Craybas defeated Lenka Nemeckova 7-6 6-2 in the Midland MI 75K round of 32 on hard. The upset overturned the form book — Lenka Nemeckova came in leading the head-to-head 1–0. Jill Craybas claimed a first win over Lenka Nemeckova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-09-28 | Santa Clara 75K | R32 | hard | Lenka Nemeckova | 2-6 6-0 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.