Marco Monnecchi defeated Gabrio Castrichella 6-4 2-6 6-4 in the Italy 3 Masters 4 round of 32 on clay. The upset overturned the form book — Gabrio Castrichella came in leading the head-to-head 1–0. Marco Monnecchi claimed a first win over Gabrio Castrichella in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-04-06 | Italy 1 Masters 1 | R32 | clay | Gabrio Castrichella | 7-6 6-3 |