Filippo Leonardi defeated Omar Giacalone 5-7 6-2 6-3 in the Italy F20 round of 16 on clay. The result followed the form book — Filippo Leonardi came in leading the head-to-head 2–1. Filippo Leonardi extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2017-07-10 | Italy F21 | R16 | clay | Filippo Leonardi | 7-6(3) 6-0 |
| 2015-04-27 | Italy F7 | SF | clay | Omar Giacalone | 6-4 7-6(4) |
| 2011-08-29 | Italy F25 | R16 | clay | Filippo Leonardi | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.