Gilles Simon defeated Andy Roddick 6-3 6-3 in the Rome Masters round of 64 on clay. The upset overturned the form book — Andy Roddick came in leading the head-to-head 2–1. Gilles Simon narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-08-01 | Washington | R16 | hard | Gilles Simon | 6-3 6-3 |
| 2008-10-26 | Paris Masters | R16 | hard | Andy Roddick | 6-3 7-5 |
| 2007-03-19 | Miami Masters | R32 | hard | Andy Roddick | 6-4 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.