All of Emma Raducanu, Andy Murray and Kyle Edmund saw their runs at the Miami Open end prematurely with first-round defeats on Wednesday.
A second set fightback from Raducanu was in vain as she went down to Canada's Bianca Andreescu, while Murray and Edmund were knocked out by Dusan Lajovic and Wu Yibing respectively.
Former world number four Andreescu took two hours and 33 minutes to close a tantalising battle with Raducanu 6-3 3-6 6-2, having stormed into a 3-0 lead with an early break in the opening set.
Raducanu asked few questions on Andreescu's serve as the Canadian comfortably held for a 1-0 lead, but after wasting seven break points in the second set, the British number one converted her eighth for a 5-3 lead.
Raducanu saw out a hold to 15 to force a third set, and despite immediately going 40-0 up on Andreescu's serve, the former US Open champion could not take any of those break points in the turning point of the match.
After a pair of opening holds each, Andreescu found her groove to embark on a four-game winning streak, sealing her place in the second round after a hard-fought contest.
Meanwhile, Murray - whose magnificent comebacks have become a staple of his 2023 season so far - could not produce a similar response against Lajovic, who prevailed 6-4 7-5 in one hour and 36 minutes.
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The world number 76 brought out the winners in force to break to love in the seventh game of the match, and a couple of unforced errors bedevilled Murray as he ceded the first set.
A tight second set saw eight holds traded between the two men before more Murray mishitting proved costly, as Lajovic broke in the ninth game to present himself with the chance to serve out the match.
However, Murray unsurprisingly refused to throw in the towel and broke straight back to level the second set at 5-5, but Lajovic took advantage of more errors from the Brit to break once more before seeing out a nervy hold to advance.
It was a similar story for Edmund, who fell to a 5-7 5-7 loss to China's Yibing in one hour and 34 minutes, having been made to pay for a mistake-laden start with three double faults in his opening two service games.
Yibing earned the first break of the match for a 3-1 lead on one of those double faults, although Edmund broke back in the ninth game while Yibing was serving for the set.
However, another untimely double fault on set point allowed Yibing to take control of the match, and the Chinese 23-year-old established a 3-0 lead in the second set.
Once again, Edmund broke back in the ninth game to keep the contest alive, but Yibing soon cut out the unforced errors to dump the Briton out and set up a tie with Argentina's Diego Schwartzman.
