Massimo Ocera defeated Simone Bolelli 6-4 3-6 6-2 in the Italy F17 round of 16 on clay. Massimo Ocera extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-11-01 | Belgium F2 | R32 | hard | Massimo Ocera | 7-5 6-2 |
| 2003-05-26 | Italy 2 1 | R32 | clay | Simone Bolelli | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.