Ivan Cerovic defeated Filippo Leonardi 6-2 6-4 in the Italy F10 round of 32 on clay. The upset overturned the form book — Filippo Leonardi came in leading the head-to-head 1–0. Ivan Cerovic claimed a first win over Filippo Leonardi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-10-06 | Italy F34 | R32 | hard | Filippo Leonardi | 7-5 7-6(3) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.