Nahuel Fracassi defeated Giancarlo Petrazzuolo 5-3 4-2 1-4 5-3 in the Italy F9 round of 32 on clay. The upset overturned the form book — Giancarlo Petrazzuolo came in leading the head-to-head 2–0. Nahuel Fracassi claimed a first win over Giancarlo Petrazzuolo in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-07-19 | Italy F17 | R16 | clay | Giancarlo Petrazzuolo | 4-6 6-0 6-1 |
| 2000-08-21 | Italy 4 1 | R16 | clay | Giancarlo Petrazzuolo | 6-2 6-2 |