Riccardo Ciruolo defeated Marco Monnecchi 6-1 6-1 in the Italy 1 Masters 4 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 |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 2 | R16 | clay | Riccardo Ciruolo | 6-1 6-4 |