Andy Murray lost an epic lasting three hours and 27 minutes as the former world number one’s final Miami Open appearance came to an end against Tomas Machac in the third-longest contest ever played at the tournament.
The 36-year-old recovered from 3-0 down in the deciding third set to force a tie break and saved match point before eventually succumbing to the 23-year-old in the last 32.
Murray had said he wanted to provide action on and off the court even if he lost and the Scot lived up to his ambitions, including a row with umpire Carlos Bernardes over fans moving in between points.
The two-time Wimbledon champion also required attention on an ankle issue, having admitted before the match that the physical demands of his remarkably durable career – he has now played 996 times on the ATP Tour – were impacting him.
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“It was like a Davis Cup match because the crowd was for Andy,” the Czech said afterwards.
“I understand that he’s a great player, so I was expecting that. It was a really tough match mentally because the emotions were going up and down.
“He’s managed to win lots of matches from match-point down, so it’s tough to describe the emotions now.”
British number one Cameron Norrie was knocked out in straight sets by world number four Daniil Medvedev and Australian Open champion Jannik Sinner came back from a set behind to beat the Netherlands’ Tallon Griekspoor.
Miami Open results: Osaka out
Seventh seed Casper Ruud secured a routine win over Davidovich Fokina but there was a shock for 14th seed Ugo Humbert, who lost in three sets to world number 50 Dominik Koepfer.
World number seven Holger Rune won only two games on his way to being ousted by Fabian Marozsan, an opponent ranked 50 places below him.
In the women’s draw, four-time Grand Slam title winner Naomi Osaka lost 7-6, 7-5 to Caroline Garcia, who will play Coco Gauff next.
Top-ranked Iga Swiatek lost a first-set tie break – the first of the Pole’s last 14 sets she had dropped – before seeing off 26th seed Linda Noskova.