Andrea Capodimonte defeated Stefano Cobolli 6-0 6-0 in the Italy 3 2 round of 16 on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 2–0, but Andrea Capodimonte had been the form player, winning 3 of their last 8 on clay. Andrea Capodimonte claimed a first win over Stefano Cobolli in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Italy F1 | QF | clay | Stefano Cobolli | 6-3 6-3 |
| 1999-05-11 | Italy F7 | R32 | clay | Stefano Cobolli | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.