Riccardo Ciruolo defeated Paolo Lorenzi 6-1 6-2 in the Italy F15 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 1 | R16 | clay | Riccardo Ciruolo | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.