Massimo Ocera defeated Stefano Cobolli 4-6 7-6 7-6 in the Italy F15 round of 32 on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 1–0, but Massimo Ocera had been the form player, winning 6 of their last 8 on clay. Massimo Ocera claimed a first win over Stefano Cobolli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-23 | Italy 3 2 | R16 | clay | Stefano Cobolli | 7-6(6) 6-3 |