Gilles Simon defeated Roger Federer 2-6 7-5 6-4 in the Canada Masters round of 32 on hard. The upset overturned the form book — Roger Federer came in leading the head-to-head 7–1, defending last year's final. Gilles Simon narrowed the head-to-head to 7–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2018-10-22 | Basel | QF | hard | Roger Federer | 7-6(1) 4-6 6-4 |
| 2015-06-29 | Wimbledon | QF | grass | Roger Federer | 6-3 7-5 6-2 |
| 2014-10-05 | Shanghai Masters | F | hard | Roger Federer | 7-6(6) 7-6(2) |
| 2013-05-27 | Roland Garros | R16 | clay | Roger Federer | 6-1 4-6 2-6 6-2 6-3 |
| 2013-05-12 | Rome Masters | R16 | clay | Roger Federer | 6-1 6-2 |
| 2011-03-23 | Miami Masters | QF | hard | Roger Federer | 3-0 RET |
| 2011-01-17 | Australian Open | R64 | hard | Roger Federer | 6-2 6-3 4-6 4-6 6-3 |
| 2008-11-09 | Masters Cup | RR | hard | Gilles Simon | 4-6 6-4 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 (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About