Nina Duebbers defeated Jana Hlavackova 6-3 2-6 6-4 in the Juarez 25K round of 32 on clay. The upset overturned the form book — Jana Hlavackova came in leading the head-to-head 1–0. Nina Duebbers claimed a first win over Jana Hlavackova in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-06 | Salgau 10K | R32 | clay | Jana Hlavackova | 6-3 6-1 |