Antonio Comporto defeated Stefano Valenti 6-1 6-1 in the Italy F20 round of 32 on clay. The upset overturned the form book — Stefano Valenti came in leading the head-to-head 1–0. Antonio Comporto claimed a first win over Stefano Valenti in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-22 | Italy F16 | QF | clay | Stefano Valenti | 6-4 6-2 |