Andrea Serra defeated Massimo Ocera 6-1 6-4 in the Italy 6 2 round of 32 on clay. The upset overturned the form book — Massimo Ocera came in leading the head-to-head 1–0. Andrea Serra claimed a first win over Massimo Ocera in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-06-26 | Italy F20 | R32 | clay | Massimo Ocera | 5-7 7-6(5) 6-4 |