John E. Sokolowski-USA TODAY Sports

Tommy Paul and Alex de Minaur upset the top two seeds Friday in the National Bank Open quarterfinals in Toronto.

The unseeded de Minaur of Australia knocked out the second seed, Daniil Medvedev of Russia, in two hard-fought sets, 7-6 (7), 7-5. Paul, the 12th-seeded American, outlasted the top seed, Carlos Alcaraz of Spain, 6-3, 4-6, 6-3.

Medvedev, who had a 4-0 lead in the first-set tiebreaker before losing five of the next six points, also failed to capitalize in the second set. Neither player led the set by more than one game, but Medvedev was down 6-5 and serving to set up another tiebreaker.

The Russian fell behind and fought off one match point, but de Minaur took advantage of a second opportunity and closed out the match.

"I had to play some of my best tennis today. It has been a great week for me so far. I played the right way today. I think having played him at the end of last year gave me the confidence that I had a chance," de Minaur said, referring to a three-set win over Medvedev in the Paris Masters event in October. "I just had to play the right way, and I am extremely proud of the effort and to still be alive."

de Minaur next will take on Spaniard Alejandro Davidovich Fokina, who defeated American Mackenzie McDonald in straight sets, 6-4, 6-2.

Alcaraz, the top-rated player in the world, made 13 unforced errors to eight for Paul and six double faults to just one for the American.

It was Paul's first win over a player ranked No. 1 in the world, and he also snapped Alcaraz's 14-match winning streak.

The American referenced an earlier win over Alcaraz that occurred in Montreal last summer.

"It helps knowing that you can beat your opponent. You never want to walk on the court and be like, 'I don't know if I can beat this guy'. It's the attitude you've got to have no matter who you are playing. I would say it helped a little bit," Paul said.

Paul will face the winner of Friday's other quarterfinal, which pitted Italy's Jannik Sinner, the seventh seed, vs. France's Gael Monfils.

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