Alessandro Piccari advanced past Francesco Piccari via walkover in the Italy F10 round of 16. Alessandro Piccari narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-03-28 | Italy F6 | R16 | clay | Francesco Piccari | 6-2 6-3 |
| 2004-09-13 | Italy F24 | R32 | hard | Alessandro Piccari | 6-4 6-0 |
| 2002-07-22 | Italy 5 3 | QF | clay | Francesco Piccari | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.