Giuseppe Montenet defeated Elia Grossi 7-6 6-2 in the Italy F1 round of 16 on clay. The upset overturned the form book — Elia Grossi came in leading the head-to-head 3–0, but Giuseppe Montenet had been the form player, winning 2 of their last 6 on clay. Giuseppe Montenet claimed a first win over Elia Grossi in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-19 | Italy 3 2 | R16 | clay | Elia Grossi | 6-0 6-1 |
| 1997-06-28 | Italy 4 Masters 2 | R16 | clay | Elia Grossi | 6-2 6-3 |
| 1996-04-06 | Italy 1 Masters 4 | R16 | clay | Elia Grossi | 6-2 6-2 |