Stefano Cobolli defeated Diego Alvarez 6-3 6-4 in the Italy 2 1 round of 16 on clay. The result followed the form book — Stefano Cobolli came in leading the head-to-head 5–0. Stefano Cobolli extended the head-to-head to 6–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-09-13 | Italy F24 | R16 | hard | Stefano Cobolli | 4-6 6-3 6-3 |
| 2003-06-23 | Italy 3 4 | QF | clay | Stefano Cobolli | 6-4 7-6(2) |
| 2003-03-31 | Italy F1 | R32 | clay | Stefano Cobolli | 3-6 6-3 6-3 |
| 2003-03-03 | Italy 1 3 | R32 | clay | Stefano Cobolli | 6-7(2) 7-5 6-2 |
| 1999-08-21 | Italy 3 Masters 1 | QF | clay | Stefano Cobolli | 6-3 6-3 |