Riccardo Ciruolo defeated Giancarlo Petrazzuolo 6-1 5-7 6-1 in the Italy F2 round of 16 on clay. The result followed the form book — Riccardo Ciruolo came in leading the head-to-head 1–0. Riccardo Ciruolo extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | Italy 4 2 | R16 | clay | Riccardo Ciruolo | 7-6(2) 6-1 |