Stefanos Tsitsipas emerged from the jaws of defeat to upstage ATP Rogers Cup champion Alexander Zverev, while Rafael Nadal rallied past Marin Cilic to reach the semis.
Tsitsipas faced two match points before the in-form Greek teenager stunned Zverev in Toronto on Friday.
World number one Nadal stopped red-hot sixth seed Cilic to book his spot in the final four at the ATP 1000 tournament.
TSITSIPAS MATCHES RAFA FEAT
There is just no stopping Tsitsipas after the 19-year-old ousted second seed Zverev 3-6 7-6 (13-11) 6-4.
Tsitsipas came from 6-3 and 5-2 down to shock Zverev in his first ATP 1000 semi-final.
He also became the youngest player since Nadal in 2006 to beat three top-10 players in a single tournament, having defeated Zverev, Novak Djokovic and Dominic Thiem en route to the final four.
"Achieving such things makes me feel nice," said Tsitsipas. "I'm very proud of who I am and at this age to have these kind of results, which I never expected. I always thought it's going to be take more years for this to happen. But with the hard work that I've been doing, it's no surprise to me. I believe I have the game to compete against these players. I'm feeling very confident."
It does not get any easier with world number six Kevin Anderson awaiting in the semis.
NADAL OUTLASTS CILIC
The 17-time grand slam champion battled to a 2-6 6-4 6-4 win over Australian Open runner-up Cilic.
Nadal was overpowered and outplayed in the opening set as Cilic looked set to advance to the Toronto semis.
That was before Nadal – seeking his 33rd title – stood tall to survive as the Spanish star became the first singles player to secure his spot at the ATP Finals in London.
"It means a lot to me to be in the semi-finals," said Nadal. "It's because it was a very important match for me. Being in the semi-finals is great news at the start of the hard court season. And winning three good matches in the first Masters 1000 is so important for me."
A three-time Canadian champion, Nadal will face Karen Khachanov after the Russian accounted for Robin Haase 6-3 6-1.
ANDERSON TRUMPS DIMITROV
South African fourth seed Anderson overcame a poor head-to-head record to move past Grigor Dimitrov 6-2 6-2.
Wimbledon finalist Anderson had lost six of his seven meetings against fifth seed Dimitrov before Friday's victory.
"I felt I played really well right from the beginning," Anderson said. "I think I played some really good tennis in the last couple of matches, just not from the start... I felt I was in a really good frame of mind, playing the kind of tennis that I knew I wanted to be playing and needed to be playing."
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