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Leylah Annie Fernandez of Canada serves to Ashlyn Krueger of the U.S. at the National Bank Open in Toronto on Aug. 8.Frank Gunn/The Canadian Press

Leylah Fernandez had an opening.

Trailing her second-round match 5-4 in the first set at the National Bank Open, the Canadian tennis star had worked hard to secure five break-point opportunities.

Five chances – including three at love-40 – to get back on serve turned into five wasted moments.

Fernandez never recovered.

The 21-year-old from Laval, Que., ranked 25th in the world was upset 6-4, 6-2 by American qualifier Ashlyn Krueger on Thursday to crash out of her country’s signature event.

“It wasn’t the prettiest match, it wasn’t the greatest match,” said a still-seething Fernandez, the last Canadian remaining in the singles field, including the men’s bracket in Montreal. “I wasn’t able to take advantage of the points that were given to me.

“I should have been more offensive, and I wasn’t. I wasn’t there mentally, I wasn’t there physically.”

The No. 15 seed, who declined to speak with reporters until more than 5 1/2 hours had passed following the loss, got a small measure of revenge alongside younger sister Bianca with a doubles victory over Krueger and American partner Catherine Harrison later Thursday.

After splitting the two sets, the Canadian siblings won 11-9 in a match tiebreak to move onto the quarter-finals.

“My sister was the boss,” said the elder Fernandez, who made the 2021 U.S. Open final. “She did an amazing job in snapping me out of my little rut.”

Marina Stakusic, a 19-year-old wild card from Mississauga, Ont., was also eliminated in singles after getting thumped 6-0, 6-2 by Taylor Townsend of the U.S. on an overcast day at Sobeys Stadium.

No. 1 seed Coco Gauff, meanwhile, cruised past Yafan Wang 6-4, 6-2.

The 20-year-old American, who won last year’s U.S. Open and was coming off a third-round showing on clay at the Paris Olympics following the grass season, played her first hard-court match since April.

“It’s not easy transitioning from all these different surfaces in such a short amount of time,” Gauff said. “Happy to get pushed through.”

No. 2 Aryna Sabalenka, the two-time defending Australian Open champion, topped Yue Yuan 6-2, 6-2 to advance.

“I wouldn’t say that I played my best tennis,” said Sabalenka, who lost to Gauff in the 2023 U.S. Open final. “Really happy that I was able to stay focused no matter what.”

Other seeds advancing at the US$3.2-million event were No. 4 Jelena Ostapenko, No. 5 Daria Kasatkina, No. 6 Liudmila Samsonova, No. 8 Emma Navarro, No. 10 Anna Kalinskaya, No. 11 Marta Kostyuk, No. 12 Victoria Azarenka, No. 13 Beatriz Haddad Maia and No. 14 Diana Shnaider.

No. 7 Madison Keys retired from her match with a thigh injury, while wild-card entry and former world No. 1 Naomi Osaka lost in straight sets to Elise Mertens.

Toronto tournament director Karl Hale tried to put a positive spin on an event that had already dealt with a number of withdrawals last week – led by the top-ranked Iga Swiatek – before the Canadians all crashed out in singles, including 2019 winner and Mississauga product Bianca Andreescu.

“This is the greatest show in women’s sport,” said Hale, who added Olympic bronze medalist Gabriel Dabrowski of Ottawa is competing in doubles. “That’s what happens on the WTA Tour – you just never know.”

Krueger picked up a break in the first game of the second set against Fernandez and led 3-1 before holding to go up 4-2 thanks to some terrific serving.

“Fun environment,” the 82nd-ranked American said of the partisan crowd. “Turned it around and acted like everyone was cheering for me.”

Krueger took a 5-2 edge on Fernandez, who didn’t register a break for the first time since last year’s third-round NBO defeat in Montreal, before finishing things off on a third match point.

The 20-year-old won 71.7 per cent of her first-serve points compared to 59.5 per cent for Fernandez.

“These courts really help my serve,” said Krueger, who lost to Fernandez on grass in their only other meeting. “I’ve been taking a lot of opportunities to come forward because they’re faster.”

Stakusic, meanwhile, showed some life in the second set by winning two games and getting back on serve against Townsend, but the world No. 160 couldn’t keep the momentum going against the 71st-ranked American.

Edmonton’s Mia Kupres and Ariana Arseneault of Richmond Hill, Ont., advanced to the doubles quarter-finals without swinging a racket because of an opponent’s injury.

The NBO men’s singles competition at IGA Stadium in Montreal saw its remaining Canadians ousted Wednesday when stars Felix Auger-Aliassime and Denis Shapovalov were both eliminated.

Hale, however, isn’t sounding alarm bells regarding the state of tennis in this country because of one high-profile – and disappointing – week.

“There’s ebbs and flows in their careers,” he said of Canada’s stable of talent. “You’ll see Denis, Felix, Leylah, Bianca start to move forward again.”

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