Nikolay Davydenko defeated Gilles Simon 2-6 6-1 6-1 in the Canada Masters round of 64 on hard. The upset overturned the form book — Gilles Simon came in leading the head-to-head 5–2, defending last year's round of 32. Nikolay Davydenko narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2011-10-31 | Valencia | R32 | hard | Nikolay Davydenko | 6-4 4-6 6-3 |
| 2011-02-14 | Marseille | R32 | hard | Gilles Simon | 7-6(6) 6-4 |
| 2010-10-31 | Valencia | QF | hard | Gilles Simon | 6-4 6-7(5) 6-3 |
| 2009-08-16 | Cincinnati Masters | R16 | hard | Gilles Simon | 6-7(6) 6-4 6-4 |
| 2007-08-19 | New Haven | R16 | hard | Gilles Simon | 6-4 6-4 |
| 2007-07-23 | Umag | R32 | clay | Gilles Simon | 6-2 2-6 6-3 |
| 2007-05-14 | Hamburg Masters | R32 | clay | Nikolay Davydenko | 6-7(5) 6-4 7-5 |
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 (54 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About