Giuseppe Montenet defeated Massimo Bertolini 6-3 6-0 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 |
|---|---|---|---|---|---|
| 1997-08-02 | Italy 5 Masters 2 | R16 | clay | Massimo Bertolini | 3-0 |
| 1996-08-03 | Italy 4 Masters 2 | R32 | clay | Giuseppe Montenet | 6-1 6-4 |