Tim Henman defeated Guillermo Canas 3-6 7-6 6-2 in the Canada Masters round of 32 on hard. The upset overturned the form book — Guillermo Canas came in leading the head-to-head 6–0. Tim Henman claimed a first win over Guillermo Canas in seven meetings, narrowing the head-to-head to 6–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-03-19 | Miami Masters | R128 | hard | Guillermo Canas | 3-6 6-2 6-1 |
| 2005-03-07 | Indian Wells Masters | QF | hard | Guillermo Canas | 7-6(1) 7-5 |
| 2004-01-19 | Australian Open | R32 | hard | Guillermo Canas | 6-7(5) 5-7 7-6(3) 7-5 9-7 |
| 2001-10-08 | Vienna | R16 | hard | Guillermo Canas | 3-6 7-6(4) 7-6(5) |
| 2001-05-28 | Roland Garros | R32 | clay | Guillermo Canas | 4-6 6-4 6-4 3-6 7-5 |
| 1999-08-30 | US Open | R128 | hard | Guillermo Canas | 7-6(1) 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.