Seven-time Wimbledon champion Roger Federer was beaten 2-6 7-6 (10-8) 6-4 by 39-year-old Tommy Haas on grass at the Stuttgart Open.
The Swiss, playing his first match in two months, won the first set but succumbed to the German in the second-set tie-break having had match point.
"It's always special to play a close friend like Roger on grass, always lots of emotion," said the world 302.
The loss was only the second this year for Federer, who owns 2017 titles at the Australian Open, Indian Wells and Miami.
The 18-time grand slam winner last played on April 2, when he won Miami; he then skipped the entire clay season to prepare for the grass and Wimbledon.
Haas produced only his fourth win in 17 matches against his longtime friend, in a series which began in 2000.
'I'm mainly speechless of course,' Haas said.
'Playing Roger is very special - especially on grass and also in Germany.'
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