Giancarlo Petrazzuolo defeated Elia Grossi 6-3 4-6 6-4 in the Italy 3 Masters 1 round of 32 on clay. The upset overturned the form book — Elia Grossi came in leading the head-to-head 3–0, but Giancarlo Petrazzuolo had been the form player, winning 3 of their last 6 on clay. Giancarlo Petrazzuolo claimed a first win over Elia Grossi in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-07-24 | Italy F8 | R16 | clay | Elia Grossi | 4-0 4-1 4-0 |
| 2000-06-19 | Italy 3 3 | R32 | clay | Elia Grossi | 6-7(4) 6-3 6-1 |
| 2000-03-11 | Italy 1 Masters 2 | QF | clay | Elia Grossi | 6-2 1-6 6-1 |