Stefano Cobolli defeated Guillermo Carry 6-7 6-3 6-1 in the Italy 2 1 qualifying round on clay. The upset overturned the form book — Guillermo Carry came in leading the head-to-head 1–0. Stefano Cobolli claimed a first win over Guillermo Carry in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-09 | Italy F12 | R32 | clay | Guillermo Carry | 7-6(6) 3-6 6-3 |