Andy Murray was beaten 6-3 6-4 by Carlos Alcaraz in the round of 16 at the Vienna Open on Wednesday.
Murray, who edged past world number 10 Hubert Hurkacz to reach the second round of the tournament, was unable to find his best first serve against Alcaraz who continues to impress on the biggest stage.
The 18-year-old becomes the first Spaniard to beat Murray in Vienna, and was fresher and faster than the former world number one who continues to struggle on his return from injury.
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Alcaraz takes the first quarter-final spot in Austria, with the world number 38 enjoying a breakthrough season on the tour, having reached the quarter-finals of the US Open in September.
Murray beaten by fresh legs of impressive Alcaraz
Ten of Andy Murray's last 11 sets have lasted more than 50 minutes and, after his marathon encounter with Hurkacz, a win against Alcaraz looked a step too far for the two-time Wimbledon champion.
The first set was a test of baseline dominance, with Murray rolling back the years and looking near his best with some vintage groundstrokes.
A lengthy exchange of breaks dragged the first five games to the 45-minute mark, and from then Alcaraz looked the more likely to take advantage.
Carlos Alcaraz y Andy Murray (ATP Viena)
Image credit: Getty Images
The young Spaniard was suddenly able to find winners from the baseline, and his speed and movement ultimately saw him steal away the last three games to take the set.
The second set followed a similar pattern.
Murray snatched the first break and almost had the second but for some resilient baseline defending from Alcaraz.
And with Murray unable throughout the match to truly find his first serve, Alcaraz snatched a break back and levelled the second set.
At 5-4 up, Alcaraz had Murray serving to stay in the match, but a series of heavy-hitting forehands against the tiring Briton handed him the set and match.
He becomes the second-youngest player to defeat Murray, and reaches the first ATP 500 tournament quarter-final of his career.
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