Oxfordshire star Tim Henman crashed out of the Masters Series event in Toronto at the first hurdle.
Henman, seeded 15th, went down 6-4, 3-6, 6-3 to Chile's Marcelo Rios.
The British No 1 from Weston-on-the-Green was made to pay for 33 unforced errors and four double faults.
He had won his last two meetings with Rios, currently ranked 32 in the world, but never managed to hit top gear.
Rios broke Henman's serve in the sixth game of the deciding set and looked set for a comfortable victory when going 40-0 up at 5-3.
Henman rallied to save three match points but it was to no avail as Rios held his nerve to clinch the win.
Fellow Briton Arvind Parmar, who only qualified as a 'lucky loser', did well to take US Open winner Pat Rafter to three sets before going down 6-1, 4-6, 6-3.
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