Emma Raducanu crashed out of the Linz Open following a marathon 6-1 6-7(0) 7-5 defeat to Xinyu Wang in Austria.
US Open champion Raducanu was broken three times as she lost the opening set but battled back to win the second on a tiebreak.
Break-point opportunities were at a premium in the final set, however, Wang took two that came her way and wrapped up victory in two hours and 36 minutes.
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Raducanu came into the match as the top seed but it was Wang who made all of the early running in Linz.
The world number 106 created eight break point opportunities in the opening set, winning on the Raducanu serve in the third, fifth and seventh games to take the first stanza 6-1.
Raducanu had not put any pressure on her opponent’s serve in that opening set but broke in the first game of the second to hint at a comeback.
The Brit was broken immediately though, and then had to save two break points in her next service game to prevent going 3-1 down.
In the end, Raducanu held and then broke Wang, but having established a 4-2 lead she lost the eighth game of the set on her own serve to let her opponent back in.
Raducanu twice had to serve to remain in the match, which she did to force a tiebreak which she went on to win 7-0.
The third set went with serve until the ninth game when Wang converted the first break point opportunity of the set.
Wang had two opportunities to serve out the match but failed to convert. Having been broken, though, she then won the next game on the Raducanu serve before completing victory.
The Chinese player will now face Alison Riske in the quarter-finals, after the American beat Alize Cornet 6-4 6-4.
Former world number one Simona Halep also booked her place in the last eight on Tuesday, beating Aliaksandra Sasnovich 7-5 6-3 in Linz.
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