Gianluca Luddi defeated Giuseppe Montenet 6-3 6-4 in the Italy 2 Masters 4 semi-final on clay. The upset overturned the form book — Giuseppe Montenet came in leading the head-to-head 3–0, but Gianluca Luddi had been the form player, winning 6 of their last 10 on clay. Gianluca Luddi claimed a first win over Giuseppe Montenet in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-06-27 | Italy 2 Masters 3 | QF | clay | Giuseppe Montenet | 6-2 6-4 |
| 1997-08-02 | Italy 5 Masters 3 | QF | clay | Giuseppe Montenet | 3-6 6-0 6-1 |
| 1997-04-05 | Italy 2 Masters 2 | R16 | clay | Giuseppe Montenet | 6-4 6-0 |