Riccardo Ciruolo defeated Pietro Angelini 7-5 3-6 7-5 in the Italy 2 Masters 3 round of 16 on clay. Riccardo Ciruolo extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-04-06 | Italy 1 Masters 1 | R32 | clay | Riccardo Ciruolo | 7-6 6-3 |
| 1994-07-02 | Italy 2 Masters 4 | R32 | clay | Pietro Angelini | 6-2 6-2 |