Guillermo Canas defeated Gilles Simon 6-2 6-1 in the Umag quarter-final on clay. The upset overturned the form book — Gilles Simon came in leading the head-to-head 2–0. Guillermo Canas claimed a first win over Gilles Simon in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-08-11 | Beijing Olympics | R32 | hard | Gilles Simon | 7-5 6-1 |
| 2007-05-07 | Rome Masters | R32 | clay | Gilles Simon | 7-6(4) 6-4 |
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 (118 vs 200). ATP, WTA & Challenger.