Riccardo Ciruolo defeated Giuseppe Montenet 6-2 6-4 in the Italy 1 Masters 1 round of 16 on clay. The upset overturned the form book — Giuseppe Montenet came in leading the head-to-head 1–0, but Riccardo Ciruolo had been the form player, winning 2 of their last 4 on clay. Riccardo Ciruolo claimed a first win over Giuseppe Montenet in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-04-06 | Italy 1 Masters 1 | R16 | clay | Giuseppe Montenet | 6-1 1-6 6-4 |