Stefano Cobolli defeated Massimo Ocera 7-6 6-3 in the Italy 3 2 round of 16 on clay. The upset overturned the form book — Massimo Ocera came in leading the head-to-head 1–0. Stefano Cobolli claimed a first win over Massimo Ocera in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-30 | Italy F15 | R32 | clay | Massimo Ocera | 4-6 7-6(6) 7-6(5) |