Francesco Piccari defeated Luca Vanni 6-7 6-2 7-5 in the Italy F20 qualifying round on clay. The upset overturned the form book — Luca Vanni came in leading the head-to-head 2–1, but Francesco Piccari had been the form player, winning 3 of their last 4 on clay. Francesco Piccari narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-05-03 | Italy F7 | R16 | clay | Luca Vanni | 6-3 6-2 |
| 2009-10-12 | Italy F32 | R16 | clay | Francesco Piccari | 7-5 6-3 |
| 2006-08-07 | Italy F26 | SF | clay | Luca Vanni | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.