Gabrio Castrichella defeated Massimo Ardinghi 6-3 7-5 in the Italy 3 Masters 2 qualifying round on clay. The upset overturned the form book — Massimo Ardinghi came in leading the head-to-head 1–0. Gabrio Castrichella claimed a first win over Massimo Ardinghi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-04-06 | Italy 1 Masters 3 | QF | clay | Massimo Ardinghi | 6-1 6-4 |