Riccardo Ciruolo defeated Stefan Pircher 6-3 7-5 in the Italy F16 round of 32 on clay. The result followed the form book — Riccardo Ciruolo came in leading the head-to-head 2–0. Riccardo Ciruolo extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 1 | R32 | clay | Riccardo Ciruolo | 6-3 6-3 |
| 1999-06-19 | Italy 2 Masters 4 | QF | clay | Riccardo Ciruolo | 6-3 7-5 |