Claudio Grassi defeated Francesco Piccari 6-4 7-6 in the Italy F23 final on hard. The upset overturned the form book — Francesco Piccari came in leading the head-to-head 4–0. Claudio Grassi claimed a first win over Francesco Piccari in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-09-14 | Italy F28 | QF | hard | Francesco Piccari | 6-4 7-6(4) |
| 2009-08-10 | Italy F23 | R32 | clay | Francesco Piccari | 7-6(4) 3-6 7-5 |
| 2008-06-02 | Italy F16 | QF | clay | Francesco Piccari | 7-5 6-3 |
| 2007-06-04 | Italy F17 | R32 | clay | Francesco Piccari | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.