Guillermo Canas defeated Roger Federer 7-6 7-5 in the Canada Masters round of 64 on hard. The upset overturned the form book — Roger Federer came in leading the head-to-head 3–2. Guillermo Canas narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-05 | Rome Masters | R32 | clay | Roger Federer | 6-3 6-3 |
| 2007-10-15 | Madrid Masters | R16 | clay | Roger Federer | 6-0 6-3 |
| 2007-03-19 | Miami Masters | R16 | hard | Guillermo Canas | 7-6(2) 2-6 7-6(5) |
| 2007-03-05 | Indian Wells Masters | R64 | hard | Guillermo Canas | 7-5 6-2 |
| 2005-03-07 | Indian Wells Masters | SF | hard | Roger Federer | 6-3 6-1 |
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