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Kyle Edmund's Madrid Open run ended by Denis Shapovalov at quarter-final stage

Shapovalov, 19, aiming to become youngest Masters 1000 finalist since Richard Gasquet in 2005

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Highlights of Denis Shapovalov up against Kyle Edmund in the quarter-finals of the Madrid Open

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 on Friday evening.

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 in the Spanish capital.

World No 43 Shapovalov, the youngest player in the top 100, will face Alexander Zverev in Saturday's semi-final 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 - live on Sky Sports.

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There was a controversy during Kyle Edmund's match with Denis Shapovalov after a fan shouted during Shapovalov serve. Edmund didn't return and it went down as an ace much to Edmund's fury...

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.

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"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.

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Denis Shapovalov told Sky Sports that he felt awful over the controversial call that happened during the second set in his win over Kyle Edmund

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.

Shapovalov will face Germany's Zverev in the last four on Saturday after the 21-year-old came through his quarter-final against big-serving American John Isner, fresh off his first Masters title in Miami, in straight sets 6-4 7-5.

Zverev managed to break the American's serve at 5-5 in the second set and held his nerve to serve out the match in two sets.

The Masters 1000 Series continues throughout this week with our coverage of the ATP Madrid Open semi-finals on Sky Sports Arena starting from 3pm on Saturday.

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