Nahuel Fracassi defeated Alessandro Piccari 3-6 6-4 6-1 in the Italy F1 round of 32 on clay. The result followed the form book — Nahuel Fracassi came in leading the head-to-head 1–0. Nahuel Fracassi extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 3 | R32 | clay | Nahuel Fracassi | 7-5 7-5 |