Stefano Mocci defeated Riccardo Ciruolo 6-4 6-2 in the Italy 4 3 round of 32 on clay. The upset overturned the form book — Riccardo Ciruolo came in leading the head-to-head 1–0. Stefano Mocci claimed a first win over Riccardo Ciruolo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-09-18 | Italy F11 | R32 | hard | Riccardo Ciruolo | 6-3 6-4 |