Giancarlo Petrazzuolo defeated Daniele Giorgini 2-6 7-6 7-6 in the Italy F25 qualifying round on hard. The upset overturned the form book — Daniele Giorgini came in leading the head-to-head 3–1. Giancarlo Petrazzuolo narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-08-14 | Italy F27 | QF | clay | Giancarlo Petrazzuolo | 6-3 6-3 |
| 2006-02-27 | Italy F3 | F | clay | Daniele Giorgini | 7-6(1) 6-4 |
| 2003-09-22 | Italy F10 | QF | hard | Daniele Giorgini | 7-6(2) 3-6 6-3 |
| 2002-09-30 | Italy 7 3 | R16 | clay | Daniele Giorgini | 6-3 4-6 6-3 |