Giacomo Oradini defeated Filippo Leonardi 7-5 6-2 in the Italy F2 round of 32 on hard. The upset overturned the form book — Filippo Leonardi came in leading the head-to-head 2–0. Giacomo Oradini claimed a first win over Filippo Leonardi in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-09-30 | Italy F28 | R32 | clay | Filippo Leonardi | 6-4 6-2 |
| 2012-04-09 | Italy F4 | R32 | clay | Filippo Leonardi | 6-3 6-4 |