Riccardo Ciruolo defeated Rodrigo Monte 6-3 6-0 in the Italy F6 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 |
|---|---|---|---|---|---|
| 1999-08-09 | Italy F16 | F | clay | Riccardo Ciruolo | 6-1 4-6 6-0 |