Massimo Boscatto defeated Giuseppe Montenet 6-4 6-2 in the Italy 2 Masters 3 round of 32 on clay. The upset overturned the form book — Giuseppe Montenet came in leading the head-to-head 2–0. Massimo Boscatto claimed a first win over Giuseppe Montenet in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-06-27 | Italy 2 Masters 1 | QF | clay | Giuseppe Montenet | 6-2 6-4 |
| 1996-04-06 | Italy 1 Masters 1 | R32 | clay | Giuseppe Montenet | 6-4 6-1 |