The fourth-seeded Zverev, seeking a second tournament title in as many weeks, advanced to the final on Sunday against second-seeded Roger Federer, a 6-3, 7-6 (5) victor over unseeded Robin Haase of the Netherlands. But that doesn't change things.
Federer has won of their three meetings, including a victory over the German on grass in June.
"In the juniors, yeah (and) probably my two times when I beat (Marco) Chiudinelli, because we grew up together in Basel, we played soccer against each other", Federer said.
Still moving magnificently in the week he turned 36, Federer made an ominous start by moving 2-0 ahead - taking the fifth break point that came his way in Haase's opening service game. A win will give help Federer reach his first final of the tournament since losing to Jo-Wilfried Tsonga in 2014 title match.
The youngster responded impressively to Nadal easing through the first set to force a decider, where Shapovalov saved three break points before winning an epic 14-minute third game, which included 10 deuces. "I have mixed feelings on that", he said.
"I'm looking forward to a tough match because he can serve very well and he mixes up his tactics a lot", said Federer.
Kevin Anderson eased past Sam Querrey 6-4 6-1 while Adrian Mannarino beat Hyeon Chung 6-3 6-3 and will be Shapovalov's quarter-final opponent. I think my concentration and just my playing has gone up a notch. I believe it's because today I was more aggressive coming to the net.
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The second-seeded Federer is seeking a third Rogers Cup title, but his first in Montreal, having won in 2004 and 2006 in Toronto. He would need to win here and have an equal or better finish than Rafael Nadal at the Western & Southern Open in Cincinnati next week to become the World No.1 on August 21.
The victory marks Wozniacki's first career win against a No.1 and gives the 27-year-old a 6-2 advantage in head-to-head matches with Pliskova. He really put the pressure on me.
"If I don't save those match points in the first match, there's no chance of being here".
Notably, Haase has had a good run in the tournament, beating the likes of Albert Ramos-Vinolas and Grigor Dimitrov en route to his maiden Masters 1000 semi-final.
"Rafa took a lot out of me. But, in general, to make an achievement like this is good because it shows you can do it".
Federer took the opening with both hands as he ruthlessly served out the set in the next game easily, clinching it 6-4.