Nicolas Almagro defeated Simone Bolelli 6-0 7-5 in the Rome Masters round of 64 on clay. The upset overturned the form book — Simone Bolelli came in leading the head-to-head 2–1, defending last year's round of 32. Nicolas Almagro narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-09-21 | Bucharest | R32 | clay | Nicolas Almagro | 6-4 6-3 |
| 2008-10-12 | Madrid Masters | R64 | clay | Simone Bolelli | 7-6(4) 6-1 |
| 2007-09-10 | Bucharest | R32 | clay | Simone Bolelli | 4-6 5-1 RET |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.