Kyle Edmund's hopes of reaching a first Masters 1000 semi-final were dashed at the Madrid Open as 19-year-old Denis Shapovalov prevailed 7-5 6-7 (6-8) 6-4 last night.
The British No.1 had beaten Novak Djokovic and David Goffin en route to the last eight, but Shapovalov - making his Madrid bow - put an end to Edmund's run.
World No.43 Shapovalov, the youngest player in the top 100, will face either John Isner or Alexander Zverev in today's semi-final clash as he looks to reach his first final on the ATP Tour.
Meanwhile, despite the defeat, Edmund will break into the top 20 for the first time on Monday, while he will also be in action in the Italian Open next week
Having shared out their previous four meetings, the pair were evenly matched in Madrid, trading early breaks in the opening set. However, Shapovalov pounced on the Edmund serve to edge the first set 7-5.
A tight second set followed, with Shapovalov saving two break points in the ninth game before a contentious moment in the 11th.
With Shapovalov serving at 5-5, 30-30, a noise from the crowd caused Edmund to stop as his opponent served, but despite the Briton's protests, the point was given as an ace.
"Kyle, it's not the Davis Cup, I talked to the crowd but I can't do anything," the umpire told Edmund, who then saved a match point in the following game to take it to a tie-break.
Edmund outlasted Shapovalov 8-6, but the Canadian regained his composure to claim a crucial break in the third game of the deciding set, before seeing out the match after two hours and 28 minutes on court.
Rafa Nadal suffered a shock 7-5 6-3 defeat to Austrian Dominic Thiem, a result that means the Spaniard will lose the World No.1 ranking.
Thiem was the last player to beat the Spaniard on clay - at last year's Rome Masters. Nadal had set a record of winning 50 consecutive sets on a single surface by beating Argentine Diego Schwartzman on Thursday.
Nadal's exit means Roger Federer will reclaim the number one spot on Monday.
"I haven't been good enough today," Nadal said. "He was better than me.
"Some days you don't play as good as you would like to play. Also when that happens it's because your opponent is doing really well."