Gianluca Luddi defeated Massimo Bertolini 6-3 6-4 in the Italy 4 Masters 1 round of 16 on clay. The upset overturned the form book — Massimo Bertolini came in leading the head-to-head 1–0. Gianluca Luddi claimed a first win over Massimo Bertolini in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-08-03 | Italy 4 Masters 3 | SF | clay | Massimo Bertolini | 6-1 6-4 |