James Blake defeated Florent Serra 6-4 6-1 in the Estoril quarter-final on clay. The upset overturned the form book — Florent Serra came in defending last year's semi-final. James Blake extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-02-09 | San Jose | R16 | hard | James Blake | 6-4 6-3 |
| 2007-03-19 | Miami Masters | R64 | hard | Florent Serra | 7-6(8) 2-6 6-3 |
| 2007-03-05 | Indian Wells Masters | R64 | hard | James Blake | 6-3 7-6(2) |
| 2006-05-08 | Rome Masters | R64 | clay | Florent Serra | 6-4 7-6(3) |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (150 vs 164). ATP, WTA & Challenger.