Flavio Cipolla defeated Giancarlo Petrazzuolo 6-4 6-4 in the Italy F2 round of 32 on clay. The upset overturned the form book — Giancarlo Petrazzuolo came in leading the head-to-head 2–0. Flavio Cipolla claimed a first win over Giancarlo Petrazzuolo in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-03-12 | Italy F5 | F | clay | Giancarlo Petrazzuolo | 6-3 6-4 |
| 2004-02-09 | Great Britain 1 3 | SF | hard | Giancarlo Petrazzuolo | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.