Filippo Leonardi defeated Enrico Fioravante 6-4 6-4 in the Italy F27 round of 32 on clay. The upset overturned the form book — Enrico Fioravante came in leading the head-to-head 2–1, but Filippo Leonardi had been the form player, winning 1 of their last 4 on clay. Filippo Leonardi narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2012-07-16 | Italy F18 | R32 | clay | Enrico Fioravante | 6-4 6-4 |
| 2011-09-05 | Italy F26 | QF | clay | Enrico Fioravante | 4-6 6-2 6-2 |
| 2010-10-04 | Italy F29 | R16 | hard | Filippo Leonardi | 7-6(8) 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.