Novak Djokovic played singles and doubles matches Friday but couldn’t keep Serbia from losing to Russia 2-1 in the quarterfinals of the Davis Cup.

Djokovic defeated Karen Khachanov 6-3, 6-3 in the second singles match to even the score at 1-1, then returned to the court about half an hour later to team up with Viktor Troicki in the decisive doubles match. They lost to Khachanov and Andrey Rublev 4-6, 6-4, 7-6 (8) after squandering three match points.

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Serbia's Novak Djokovic celebrates after winning Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Novak Djokovic played singles and doubles matches Friday but couldn’t keep Serbia from losing to Russia 2-1 in the quarterfinals of the Davis Cup.

Serbia's Novak Djokovic celebrates after winning Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

The result puts Russia in the Davis Cup semifinals for the first time since 2008. The Russians will next face Canada, which eliminated Australia. Russia is seeking its third Davis Cup title, and first since 2006.

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

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Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Russia's Karen Khachanov returns the ball to Serbia's Novak Djokovic during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Russia's Karen Khachanov returns the ball to Serbia's Novak Djokovic during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Rublev had put Russia ahead with a 6-1, 6-2 win over Filip Krajinovic in the first singles match.

Serbia's Novak Djokovic celebrates after winning Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic celebrates after winning Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

The result puts Russia in the Davis Cup semifinals for the first time since 2008. The Russians will next face Canada, which eliminated Australia. Russia is seeking its third Davis Cup title, and first since 2006.

Serbia, the 2010 Davis Cup champion, was trying to return to the semifinals for the first time since 2017, when the team lost to eventual champion France.

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Serbia's Novak Djokovic celebrates after winning Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic celebrates after winning Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

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Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Russia's Karen Khachanov returns the ball to Serbia's Novak Djokovic during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Russia's Karen Khachanov returns the ball to Serbia's Novak Djokovic during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)

Serbia's Novak Djokovic serves to Russia's Karen Khachanov during their Davis Cup tennis match in Madrid, Spain, Friday, Nov. 22, 2019. (AP PhotoBernat Armangue)