Guillermo Carry defeated Stefano Cobolli 7-6 3-6 6-3 in the Italy F12 round of 32 on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 1–0, but Guillermo Carry had been the form player, winning 2 of their last 8 on clay. Guillermo Carry claimed a first win over Stefano Cobolli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-05-26 | Italy 2 1 | QF | clay | Stefano Cobolli | 6-7(10) 6-3 6-1 |