Massimo Bertolini defeated Gianluca Luddi 6-1 6-4 in the Italy 4 Masters 3 semi-final on clay. The upset overturned the form book — Gianluca Luddi came in leading the head-to-head 1–0. Massimo Bertolini claimed a first win over Gianluca Luddi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-08-03 | Italy 4 Masters 1 | R16 | clay | Gianluca Luddi | 6-3 6-4 |