Simone Bolelli defeated Massimo Ocera 6-4 6-4 in the Italy 2 1 round of 32 on clay. The upset overturned the form book — Massimo Ocera came in leading the head-to-head 2–0. Simone Bolelli claimed a first win over Massimo Ocera in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-06-13 | Italy F17 | R16 | clay | Massimo Ocera | 6-4 3-6 6-2 |
| 2004-11-01 | Belgium F2 | R32 | hard | Massimo Ocera | 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.