Andy Murray blew a 4-0 lead in the deciding set and lost to Albert Ramos-Vinolas 2-6, 6-2, 7-5 in the third round of the Monte Carlo Masters on Thursday.
Former French Open and Monte Carlo champion Stan Wawrinka followed Murray out after losing to Pablo Cuevas of Uruguay 6-4, 6-4.
Meanwhile, defending champion Rafael Nadal beat Alexander Zverev, spoiling the German’s 20th birthday, 6-1, 6-1, and two-time champion Novak Djokovic overcame a Murray-like wobble before getting past Pablo Carreno Busta 6-2, 4-6, 6-4.
Djokovic dropped five straight games from 2-0 up in the second set and had to dig deep against the gritty Spaniard, whose speed across the court saw him retrieve countless shots.
Djokovic trailed 15-40 serving in the ninth game of the decider but held his nerve. The Serb sealed victory with a cross-court volley at the net.
Murray, returning from a right elbow injury which sidelined him during the Miami Open and Davis Cup quarterfinals, struggled on his serve in a scrappy match lasting more than 2 1/2 hours. The match featured 13 service breaks, including seven against Murray.
“I’m disappointed to lose from the position that I was in,” said Murray, last year’s French Open runner-up to Djokovic. “I haven’t lost many matches like that in my career.”
Ramos-Vinolas, of Spain, celebrated his first win over a world No. 1 in four chances.
Three-time Grand Slam winner Wawrinka never found his touch or range and conceded match point when his backhand pass — normally one of the best shots in men’s tennis — clipped the net and went out. Cuevas hit a sweet forehand winner down the line on the next point and raised his arms after beating Wawrinka in their first-ever meeting.