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Tim Henman crashed out of the Toronto Masters as he was beaten in straight sets by Brazilian Gustavo Kuerten.
The British number one lost 7-5 6-4 but only after spurning three break points in each set.
Henman, playing his first tournament since Wimbledon, was seeded fifth and preparing for the US Open but he struggled to deal with Kuerten's huge serve and fine groundstrokes.
The Brit had his first break point at 2-1 in the first set and two more at 5-4, but he wasn unable to take any and Kuerten broke him in the following game.
The former world number one almost won Henman's first service game in the second set but he did break serve when the French Open semi-finalist miscued a forehand.
Kuerten served out the game to win 7-5 6-4 while Henman is set to return to action in next week's Cincinnati Masters.