Carlos Poch Gradin defeated Giancarlo Petrazzuolo 6-3 7-6 in the Portugal F2 round of 32 on hard. The upset overturned the form book — Giancarlo Petrazzuolo came in leading the head-to-head 1–0. Carlos Poch Gradin claimed a first win over Giancarlo Petrazzuolo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-02-27 | Italy F3 | R16 | clay | Giancarlo Petrazzuolo | 7-6(3) 6-1 |