Andy Murray received treatment on his ankle in the deciding set before losing to inspired Czech Tomas Machac 5-7 7-5 7-6 (7-5) in an epic encounter at the Miami Open on Sunday.
After winning the opening set, 36-year-old Murray appeared to be on course for a spot in the fourth round of the tournament he has won twice previously.
But he raged at umpire Carlos Bernardes for failing to control the movement of spectators around the Butch Buchholz court as he lost his serve at the end of the second set.
Machac then raced into a 3-0 lead in the decider, although Murray battled back before receiving medical treatment following an awkward landing on his ankle at 5-5.
The former world No 1 managed to drag the contest into a tie-breaker but Machac conjured up four points in a row from 5-3 down to win a marathon encounter lasting three hours and 27 minutes.
"It's always a pleasure to share the court with such a great legend. So first of all, I'm happy that I can play this long match against him. But on the opposite, I don't want to play so long!" Machac said in his on-court interview.
"But at the end, there was everything... I pushed myself from the bottom to manage to win today."
Murray had taken the first set after finally capitalising on his ninth break point and, following a 40-minute rain delay, the second set looked destined for a tie-break until Murray lost his serve in the 12th game.
The 36-year-old's frustrations with fans moving between points boiled over and he could be heard shouting to Bernardes: "Useless, useless."
In response to an unheard reply from Bernardes, Murray responded: "What are you talking about? It's quite obvious when people are standing up between every single point."
It was no surprise that a distracted Murray then lost his serve at the start of the decider but Machac was unable to close out the match at 5-3, serving two double faults as he let Murray back into the contest.
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