Serbian Dusan Lajovic beat Andy Murray 6-4, 7-5 at the Miami Open on Wednesday, sending the Briton packing in the first round with his first hardcourt win of the season.
Lajovic thrust his fists to the air after surviving a 16-shot rally on the final point, setting up a meeting with American Maxime Cressy, who won their only prior encounter.
Lajovic drew first blood, breaking the three-times Grand Slam winner to love in the seventh game and kept the momentum going in the second set.
Up a break late in the second set, however, he squandered the advantage with a double fault and a costly unforced error in the 10th game, but found his nerve to break Murray's serve in the next game.
It was disappointing for Murray, who reached the final in Doha last month. The 35-year-old flung his racquet in frustration after a costly unforced error - one of 15 across the match - late in the affair and told reporters he had expected a better performance from himself.
"I served pretty well, but the rest of the game was a bit of a problem today. Didn't really return that well. Yeah, made a number of errors that obviously I wouldn't expect to be making," Murray said.
"Wasn't expecting to play like that, even based on the last few days because I've been decent in practice."
Frenchman Gael Monfils was forced to retire with a right wrist injury while tied 3-3 in the first set of his match against countryman Ugo Humbert.
Monfils, 36, winced in pain as he approached the net where he used his left hand to shake Humbert's hand.
It is the second consecutive first-round exit this month for Monfils, who fell to Australian Jordan Thompson in straight sets at Indian Wells.
Another Frenchman, Arthur Rinderknech, also retire injured during his first-round match against Japan's Taro Daniel.
Germany's Jan-Lennard Struff beat Italy's Fabio Fognini 6-4, 5-7 6-4 and will next face Bulgarian 21st seed Grigor Dimitrov.
Unheralded Emilio Nava overcame 15 aces from fellow American John Isner to come out on the winning side of two tiebreakers 7-6(5), 7-6(4).
The 21-year-old fired an ace of his own to set up match point and a serve Isner could not get back in play to seal the win, setting up a meeting with another American in ninth seed Taylor Fritz.
Americans JJ Wolf and Brandon Nakashima, Argentine Facundo Bagnis and Australian Alexei Popyrin were among the other players to make it out of the first round at the Masters 1000 tournament on Wednesday.
Andreescu downs Raducanu in battle of Slam winners
Canada's Bianca Andreescu beat Britain's Emma Raducanu 6-3, 3-6, 6-2 at the Miami Open on Wednesday in a first-round clash of former US Open champions looking to recapture top form after a spate of injuries.
Andreescu, coming off a third-round loss to world number one Iga Swiatek at Indian Wells, served seven aces and saved 11 of the 12 break points she faced against Raducanu to set up a clash with Greek seventh seed Maria Sakkari.
"I just came in here wanting to play my best with what I had today, I think I did that," Andreescu said during her on-court interview.
"I didn't let my negative emotions get the best of me. I stayed positive, I was very energetic and I just never gave up. Those were the keys today."
The 22-year-old Canadian broke first for a 2-0 lead when Raducanu sent a forehand long and remained in control as she closed out the opener on her fourth set point when the Briton sent a backhand into net.
Raducanu turned into the aggressor in the second set and got the edge she needed in a wild eighth game that she won on her seventh break point for a 5-3 lead before serving out the set.
In the decider, world number 31 Andreescu came back from 0-40 to hold serve in the opening game and broke for a 4-2 lead when Raducanu desperately reached for a one-handed backhand that she sent long.
With the finish line in sight, Andreescu ended the two hour, 32-minute clash on her first match point with another break when Raducanu sent a running forehand long.
Andreescu, who retired with a shoulder injury during her semi-final match at the Thailand Open in February, is still looking for her first title since the 2019 US Open.
Raducanu, who came to Miami after losing to Swiatek in the fourth round at Indian Wells, has also been plagued by injury and inconsistency since she burst onto the scene with her stunning triumph at the 2021 US Open.
In addition to the wrist injury that cut short her 2022 season, Raducanu suffered an ankle problem in the leadup to the Australian Open and tonsillitis forced her to withdraw from the Austin Open last month.
In the evening session, Shelby Rogers bounced back from an off-key second set to see off fellow American Sloane Stephens 6-4, 3-6, 6-2.
Rogers broke serve for a third time on match point to defeat Stephens and set up a meeting with second seed Aryna Sabalenka of Belarus, who beat Rogers en route to the Australian Open title in January.
Americans Sofia Kenin, Taylor Townsend, Madison Brengle and Robin Montgomery, Canada's Leylah Fernandez, China's Wang Xinyu and Czech Karolina Muchova were among those who also advanced at the WTA 1000 event on Wednesday.