Massimo Valeri defeated Giuseppe Montenet 7-6 6-2 in the Italy 2 Masters 4 semi-final on clay. Massimo Valeri extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-04-06 | Italy 1 Masters 1 | QF | clay | Giuseppe Montenet | 5-7 7-5 6-4 |
| 1995-06-03 | Italy 2 Masters 4 | R16 | clay | Massimo Valeri | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.