DOHA, Qatar — Canada's Denis Shapovalov lost 5-7, 6-3, 7-5 to American Taylor Fritz in the quarterfinals of the Qatar Open on Thursday.
The fourth-seeded Shapovalov, from Richmond Hill, Ont., saved just one of four break points against the unseeded Fritz.
The American, ranked 33rd in the world, won for the first time in four career matches against Shapovalov.
Shapovalov won all 24 of his service points in the first set before Fritz battled back.
"I don't think I have ever gone a set without winning a point on someone's serve," said Fritz. "That was kind of crazy. He was just playing really, really well in the first set. I think I just had to play myself into the match."
Shapovalov fought off two match points when trailing 5-4 in the third set, but Fritz responded to take the match.
Shapovalov was coming off a win over fellow Canadian Vasek Pospisil after getting a first-round bye.
Fritz will face Nikoloz Basilashvili of Georgia in the semifinals. Basilashvili beat No. 2 seed Roger Federer of Switzerland 3-6, 6-1, 7-5.
Federer failed to convert a match point in his second match back on tour after a 13-month injury layoff.
Basilashvili saved a match point at 5-4 in the deciding set and then broke Federer's serve in the next game.
It was a second straight grueling three-setter for Federer after his win Wednesday over Dan Evans took nearly 2 1/2 hours. The 39-year-old Federer was playing in his first tournament since the 2020 Australian Open following knee surgery.
Basilashvili has now won three consecutive tour matches for the first time since 2019.
For the first time in the 31-year history of the ATP Tour, a player reached the semifinals without hitting a ball after getting his second walkover in a row.
Russia's Andrey Rublev benefited from a first-round bye, before Richard Gasquet withdrew ahead of their second-round match. Marton Fucsovics then withdrew from their quarterfinal Thursday with a lower back injury.
Rublev will face either top-seeded Dominic Thiem or fifth-seeded Roberto Bautista Agut for a place in Saturday's final.
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