Andy Murray was knocked out of the Miami Open as he suffered a dramatic 5-7 7-5 7-6 (7-5) defeat by Tomas Machac in the last 32.
The Briton won his ninth break point to take a 6-5 lead before serving out to love to take the opening set.
Machac broke Murray for the first time at 6-5 in the second to draw level.
Murray retrieved a break in the decider and saved match point when serving to stay in the match before succumbing to defeat when he lost the tie-break.
The 36-year-old Scot had worryingly gone down with an ankle injury at the net after hitting the winner to level at 5-5 in the third set.
He received treatment from the physio and managed to continue but could not overcome a resolute Machac, who is ranked two places higher than Murray at number 60 in the world.
The 23-year-old Czech Republic player was broken when serving for the match at 5-3 up in the third but recovered his composure and, from 5-4 behind in the tie-break, impressively won three points in a row to secure victory in three hours 27 minutes.
The match had plenty of thrills and spills with the tennis on court as well as a brief rain delay in a second set in which Murray became increasingly agitated by movement in the crowd and the concern of when he looked in agony because of his ankle issue.
Meanwhile, Australian Open winner Jannik Sinner lost the first set to the Netherlands’ Tallon Griekspoor before the Italian recovered to win 5-7 7-5 6-1.
However, Denmark’s Holger Rune suffered a 6-1 6-1 defeat by Hungary’s Fabian Marozsan in 59 minutes.
