Giuseppe Montenet defeated Massimo Boscatto 6-2 6-4 in the Italy 2 Masters 1 qualifying round on clay. Giuseppe Montenet extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 3 | R32 | clay | Massimo Boscatto | 6-4 6-2 |
| 1996-04-06 | Italy 1 Masters 1 | R32 | clay | Giuseppe Montenet | 6-4 6-1 |