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Tommy Paul pulled off the biggest upset of the week in Toronto on Friday night, taking out No. 1-ranked Carlos Alcaraz in the quarterfinals of the Masters 1000 event, 6-3, 4-6, 6-3.

It’s a big milestone for the American—his first win over a No. 1.

He had already had wins over every other Top 5 ranking:

TOMMY PAUL’S CAREER TOP 5 WINS (6):
~ d. No. 1 Alcaraz in 2023 Canada QFs
~ d. No. 2 Nadal in 2022 Paris 2nd Rd
~ d. No. 3 Zverev in 2022 Indian Wells 2nd Rd
~ d. No. 4 Alcaraz in 2022 Canada 2nd Rd
~ d. No. 5 Rublev in 2021 Indian Wells 3rd Rd
~ d. No. 5 Fritz in 2023 Acapulco SFs

Perhaps even bigger: Paul is actually the first American man to defeat a reigning No. 1 in a tour-level match in almost six years.

The last U.S. man to achieve the feat was John Isner, who beat a No. 1-ranked Rafael Nadal, 7-5, 7-6 (1), in Laver Cup play in Prague on September 24th, 2017—exactly 2,147 days ago.

Just like other team events like Davis Cup, ATP Cup and United Cup, Laver Cup matches are counted as tour-level by the ATP.

Paul is now through to the semifinals of a Masters 1000 event for the first time in his career.

Paul is now through to the semifinals of a Masters 1000 event for the first time in his career.

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After bouncing back to take the second set, Alcaraz looked like he might keep that momentum going as he brought up a break point in the first game of the third set—but Paul held, stayed on serve for a few more games and then struck with a break for 4-2, and then the two held from there until it was all over.

Afterwards, Paul said he may have been a little concerned when Alcaraz started playing highlight-reel tennis in the second set.

“Halfway through the match, when he hit that tweener winner—put me on TennisTV, for sure—I thought that’s where matches switch. I was happy that two games later I got back in the match and felt comfortable, then just had to come back out in the third.

“It was just really high-level. It always is with Carlos.”

The American was also asked what the key to his victory was.

“I would say, probably, my forehand,” he replied.

“I feel like I hit my forehand the best maybe in my life today, so it was probably a pretty good time to do it.”

Paul is now through to the semifinals of a Masters 1000 event for the first time in his career. His best previous results at this level were two quarterfinals last year—first in Montreal, where he defeated Alcaraz en route before falling to Dan Evans, and then in Paris in the fall, where he fell to Stefanos Tsitsipas.