Pantelis Moschoutis defeated Massimo Bertolini 6-2 7-5 in the Italy 4 Masters 1 round of 32 on clay. The upset overturned the form book — Massimo Bertolini came in leading the head-to-head 1–0. Pantelis Moschoutis 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 | R16 | clay | Massimo Bertolini | 6-2 6-2 |