Stefano Mocci defeated Stefano Cobolli 6-2 6-3 in the Italy F5 round of 32 on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 4–0, but Stefano Mocci had been the form player, winning 2 of their last 6 on clay. Stefano Mocci claimed a first win over Stefano Cobolli in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-07-16 | Italy F8 | R32 | clay | Stefano Cobolli | 6-1 6-3 |
| 2001-06-18 | Italy 3 2 | R32 | clay | Stefano Cobolli | 2-6 7-6(5) 6-0 |
| 2000-07-31 | Italy F9 | R16 | clay | Stefano Cobolli | 4-1 4-2 5-3 |
| 1998-04-27 | Italy F5 | R32 | clay | Stefano Cobolli | 7-5 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.