Andy Murray’s struggles on the clay continued as he was beaten 6-2 7-6 (9-7) by Italian world number 164 Andrea Vavassori at the Madrid Open.
The British former world number one, 35, looked uncomfortable through the majority of the first-round match.
It is his second straight one-sided defeat on the clay after being thrashed by Alex de Minaur in Monte Carlo.
Meanwhile, Kyle Edmund is still waiting for his first ATP win this year after losing to Austria’s Dominic Thiem.
Murray has played little on the clay since returning from career-threatening hip surgery, although the 2015 Madrid champion did win two matches in the Spanish capital last year.
This year the world number 52 has been targeting a return to the French Open next month, which would be his only his second appearance at the Grand Slam tournament since he reached the semi-finals in 2017.
But the build-up will not have matched his lofty expectations.
Murray called the thrashing by Australia’s De Minaur – where he made 26 unforced errors and won just four games – “awful” and “demoralising”, adding it was one of the worst performances of his career.
Against Vavassori, who was making his debut in a Masters 1000 event, the Scot also struggled to find his rhythm and produced a lot of mistakes.
Murray saved four match points in the second-set tie-breaker – recovering one of them after planting an overhead into the net which left him crouching on the court in disbelief – but handed over the fifth with another poor volley.
Murray’s frustrations were clear. Throughout the match he regularly shouted at himself, threw his racquet at his bag after defeat was confirmed and was still shaking his head when he left the stadium.
Qualifier Vavassori, 27, said it was “a dream come true” to beat the three-time Grand Slam champion and faces Russia’s Daniil Medvedev – another former world number one and second seed – in the second round.
“I’ve followed [Murray] in all my tennis career so it is unbelievable,” he said.
“Until the second half of the second set I played the best tennis of my life and then the nerves came in. At the end it was just joy.”
Edmund, 28, is recovering from three knee operations and has lost all six ATP Tour matches in 2023 as he continues his comeback.
The former world number 14, now ranked 498th, lost 6-4 6-1 to 2020 US Open champion Thiem.
Thiem, 29, is also gradually coming back from a serious injury – a wrist problem that ruled him out for nine months – and is 93rd in the rankings.
“I love this court, I have some unbelievable memories here, and that helped me release a bit and do better and better,” said Thiem, a two-time runner-up in Madrid.
“It’s time to work again on that reputation. Once I was a tough guy to beat on clay. It’s not the case now but I’m feeling that I’m getting better and back to shape.”
Thiem will face world number five Stefanos Tsitsipas in the second round.
