Alessandro Piccari defeated Stefano Cobolli 6-4 4-6 6-4 in the Italy 3 Satellite 1 round of 16 on clay. Alessandro Piccari extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-23 | Italy F14 | R32 | clay | Alessandro Piccari | 4-6 7-6(3) 6-2 |
| 2000-03-11 | Italy 1 Masters 4 | R32 | clay | Stefano Cobolli | 6-2 6-3 |