Chris Eubanks' hopes of ending a 23-year drought of an American winning the men’s Wimbledon title came to a heartbreaking end Wednesday. 

The 27-year-old Georgia native advanced to the quarterfinal round at the All England Club after upsetting two-time Grand Slam runner-up Stefanos Tsitsipas earlier this week.

But Eubanks' road to victory ended with a grueling five-set loss to 2021 U.S. Open champion Daniil Medvedev. 

Daniil Medvedev celebrates a point during a quarterfinal match at Wimbledon

Daniil Medvedev celebrates against Christopher Eubanks of the U.S. in a men's singles quarterfinal match at Wimbledon July 12, 2023, in London.  (Mike Hewitt/Getty Images)

Eubanks won back-to-back sets after falling 6-4 in the first.

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But Medvedev quickly powered past him, taking the fourth set in a tiebreak before sealing Eubanks’ fate in the fifth set. He advanced to his fourth semifinal round at a Grand Slam and his first at Wimbledon with a 6-4, 1-6, 4-6, 7-6(4), 6-2 victory. 

Chris Eubanks backhands

Christopher Eubanks of the U.S. plays a backhand against Daniil Medvedev in a men's singles quarterfinal match at Wimbledon July 12, 2023, in London. (Shaun Botterill/Getty Images)

Eubanks entered the grass court season without a single ATP title. But, just before heading to England, he won the men’s title at the Mallorca Championships.

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A two-time NCAA All-American at Georgia Tech, Eubanks was close to ending a more than two-decade drought. The last American to win the men’s title at Wimbledon was legendary former world No. 1 Pete Sampras. 

The only pro to come close since was Andy Roddick, who was a finalist at the All England Club in 2009, 2005 and 2004, losing each time to Roger Federer. 

Christopher Eubanks walks off the court after losing a quarterfinal match at Wimbledon

Christopher Eubanks of the U.S. leaves the court following a defeat against Daniil Medvedev in a men's singles quarterfinal match at Wimbledon July 12, 2023, in London.  (Shaun Botterill/Getty Images)

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Eubanks was ranked outside the top 100 earlier this year and climbed to No. 77 just before the start of Wimbledon. After upsetting some of the game’s top-ranked players, Eubanks now ranks No. 43.