Top seed Alexander Zverev fell at his first hurdle at the MercedesCup as Dustin Brown accounted for his second-round exit.
Qualifier Brown, the man who famously beat Rafael Nadal at Wimbledon in 2015, claimed only his second ATP Tour-level win of the year – his first coming in the opening round – with a 6-4, 6-7 (3-7), 6-3 win over the German.
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“I am very, very happy,” he told ATPTour.com. “I didn’t have a good grass-court swing last year and just wanted to come and play very good tennis. Stuttgart is a little bit at altitude and I think that helped my game.
“I’ve won three very good matches, two in qualifying and one against [John] Millman. The court played a little slower today and it was tough especially against Alex, who is a very good returner. So I had to make a lot of first serves and the break in the first set helped me to gain confidence.”
Next up for Brown is Canadian Felix Auger-Aliassime after the seventh seed beat Gilles Simon of France 7-5, 6-4 in one hour and 30 minutes.
Second seed Karen Khachanov also crashed out as the world No 9 was beaten 6-4, 6-2 by Matteo Berrettini.
The Italian will face Denis Kudla for a place in the semi-final after the American caused another upset with a 7-5, 6-7 (3-7), 6-7 (3-7) win over fifth seed Gael Monfils from France.
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