Andy Murray's dreams of a first grand slam quarter-final were dashed in a five-set thriller against world number two Rafael Nadal.
The Scottish teenager won the first and third sets to lead 2-1 but could not close out the match and Nadal eventually won 6-7 (3-7) 6-4 4-6 6-3 6-1.
For long periods the pair were evenly-matched but Nadal's greater experience told in the crucial fifth set as Murray squandered a service break early on while the Spaniard won two in the first four games to put him on course for victory.
The first set, which Murray won on a tie-break, seemed a long time ago as his opponent powered his way to victory.
In that opening set the British number one had shown great character after surviving the first break point - a set point to Nadal at 6-5 - but some big first serves when he needed them most secured the tie-break.
The pair traded mini-breaks before a wild shot from Nadal gave Murray the edge at 5-3, and when the Spaniard stretched to reach a Murray lob and fired wide he had three set points.
The Scot won the set when he successfully challenged a shot which went long from his 20-year-old opponent.
The 19-year-old from Dunblane had the luxury of three break points in game two of the second set but Nadal battled back to hold.
Murray then showed great character when he found himself two break points down after a series of unforced errors in game three. Nadal was made to work hard to retrieve two arrowing first serves and Murray completed the recovery with a stunning ace, his third of the match.
The break Murray craved came in the fourth game as he forced deuce and Nadal, who has never lost to a younger opponent on the senior tour, powered a forehand low into the net.
Murray consolidated the break to go 4-1 up, coming out on top in a superb rally at 15-15 in the fifth game.
Nadal held then claimed the break back in Murray's next service game as a two-handed backhand went long, and held again to level the set at 4-4.
Murray's service game crumbled in game nine and it was apt that he conceded the crucial break with a double-fault to put Nadal in charge, and the muscular Majorcan closed out the set 6-4 on serve.
Worryingly, Murray appeared to be moving as though inhibited by an injury, possibly to his side.
Two double-faults in a row, his fifth and sixth of the match, handed Nadal a break on a plate in the third game.
Much of the fluency was now missing from Murray's game, but he doggedly hung in and won the break back to move to 3-3 when Nadal's forehand from the baseline flew long.
The next two games went with serve but at 15-30 down in the ninth the Scot missed a simple backhand volley at the net but battled back well to go 5-4 ahead.
Murray, apparently now free from injury, then had two set points on the Spaniard's next serve and needed both to claim a 2-1 lead.
Murray opened the fourth set with an ace as he raced into a 40-0 lead only to drive long and then into the net before needing a stroke of luck with a net cord to win the game.
He was 30-0 up against the Nadal serve until he drilled a forehand and two backhands into the net to allow his opponent to hold on.
Murray found himself in an even better position in the fourth game with three break points only to squander all of them and despite him earning another two on advantage the Spaniard escaped to level things up at 2-2.
He responded with a flawless service game to love but on his next serve he faced two break points at 30-40 and advantage and succumbed to the second to trail 4-3.
Nadal comfortably held his serve and took the match into a deciding set after a Murray double fault.
Murray had a chance to break immediately but sent his cross-court backhand marginally wide and then faced similar pressure on his own serve which he could not withstand as Nadal claimed an early 2-0 lead.
An error of judgement when he had two break points in the next saw the Scottish teenager play a backhand which was heading into the tramlines and his opponent recovered.
Murray appeared to lose his focus and a second break gave Nadal a 4-0 lead, which the Spaniard extended with another successful serve.
The Scot delayed the inevitable by finally making his mark on the scoreboard but the end came just before 2am local time.Reuse content