Stefano Cobolli advanced past Nicolo Cotto via walkover in the Italy 3 1 round of 16. Stefano Cobolli extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-23 | Italy 3 2 | QF | clay | Stefano Cobolli | 6-4 6-4 |
| 2000-06-12 | Italy F6 | R32 | clay | Stefano Cobolli | 6-1 6-3 |