Riccardo Capannelli defeated Stefano Cobolli 6-4 5-7 6-4 in the Italy 3 3 qualifying round on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 1–0, but Riccardo Capannelli had been the form player, winning 1 of their last 8 on clay. Riccardo Capannelli claimed a first win over Stefano Cobolli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-06-18 | Italy 3 4 | R32 | clay | Stefano Cobolli | 6-3 6-2 |