Stefano Cobolli defeated Giancarlo Petrazzuolo 7-5 6-2 in the Italy 6 1 round of 16 on clay. The upset overturned the form book — Giancarlo Petrazzuolo came in leading the head-to-head 3–1. Stefano Cobolli narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-10-25 | Italy 4 Satellite 3 | QF | clay | Giancarlo Petrazzuolo | 5-7 7-5 6-1 |
| 2003-05-26 | Italy 2 4 | R16 | clay | Stefano Cobolli | 7-6(6) 6-3 |
| 2002-06-24 | Italy 4 4 | R32 | clay | Giancarlo Petrazzuolo | 6-4 6-3 |
| 2002-05-13 | Italy F2 | R32 | clay | Giancarlo Petrazzuolo | 7-5 2-6 6-3 |