Riccardo Ciruolo defeated Stefan Pircher 6-3 7-5 in the Italy 2 Masters 4 qualifying round 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 |
|---|---|---|---|---|---|
| 1999-08-09 | Italy F16 | R32 | clay | Riccardo Ciruolo | 6-3 7-5 |
| 1999-06-19 | Italy 2 Masters 1 | R32 | clay | Riccardo Ciruolo | 6-3 6-3 |