Massimo Bertolini advanced when Giuseppe Montenet retired 3-0 in the Italy 5 Masters 2 round of 16. Massimo Bertolini claimed a first win over Giuseppe Montenet in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-04-05 | Italy 2 Masters 1 | QF | clay | Giuseppe Montenet | 6-3 6-0 |
| 1996-08-03 | Italy 4 Masters 2 | R32 | clay | Giuseppe Montenet | 6-1 6-4 |