Massimo Ocera defeated Simone Bolelli 7-5 6-2 in the Belgium F2 round of 32 on hard. Massimo Ocera extended 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 |
| 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.