Riccardo Ciruolo defeated Marco Monnecchi 6-1 6-4 in the Italy 2 Masters 2 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 |
|---|---|---|---|---|---|
| 2000-03-11 | Italy 1 Masters 4 | R16 | clay | Riccardo Ciruolo | 6-1 6-1 |