Gilles Simon defeated James Blake 3-6 6-1 6-4 in the Madrid Masters round of 32 on clay. The upset overturned the form book — James Blake came in leading the head-to-head 2–0, defending last year's round of 32. Gilles Simon claimed a first win over James Blake in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-08-11 | Beijing Olympics | R16 | hard | James Blake | 6-4 6-2 |
| 2008-07-28 | Cincinnati Masters | R32 | hard | James Blake | 6-4 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.