Alessandro Piccari defeated Stefano Cobolli 4-6 7-6 6-2 in the Italy F14 round of 32 on clay. Alessandro Piccari extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-09-27 | Italy 3 Satellite 1 | R16 | clay | Alessandro Piccari | 6-4 4-6 6-4 |
| 2000-03-11 | Italy 1 Masters 4 | R32 | clay | Stefano Cobolli | 6-2 6-3 |