Germana Di Natale defeated Nirupama Sanjeev 6-4 6-2 in the Valladolid 25K round of 32 on hard. The result followed the form book — Germana Di Natale came in leading the head-to-head 1–0. Germana Di Natale extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-19 | Gelos 25K | R32 | clay | Germana Di Natale | 6-4 6-3 |