Tsitsipas showed his nerve right from the start, as he surprised Djokovic (and everyone else watching) with a 5-2 game lead.
A confident Tsitsipas sent a blistering forehand to the back corner while the ninth-seeded Serbian was heading the other way on his first match point to secure the win before looking at his box in disbelief.
Top seed Rafa Nadal battled past Swiss wild card Stan Wawrinka 7-5, 7-6 (7-4) and will next meet Marin Cilic, who took down Argentinian Diego Schwartzman 6-3, 6-2. "And to come out and just play, I mean, that's all I wanted", said ATP World Tour Finals champion Dimitrov.
His trademark retrieving skills were on display throughout the match but Tsitsipas used strong groundstrokes to push the pace and force Djokovic to fully stretch on several rallies.
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"I thought it went really well out there", said Polansky, who's never made it past the second round of a Rogers Cup. Maybe if I played Chung it could be a little bit just having the home crowd support.
He took advantage of a Djokovic unforced error for an early break at 4-2 and used a few 210-km/h serves to take the first set by holding at love. Djokovic realised what he was up against and turned his game on in the second set, giving the crowd a real nail-biter.
Anderson topped qualifier Ilya Ivashka of Belarus 7-5, 6-3, and Dimitrov beat American Frances Tiafoe 7-6 (1), 3-6, 7-6 (4).
"I was serving well so that break was everything", Tsitsipas said. But even the Andy one, I was a little surprised by that one just because he was entered on his protected ranking, and the Federation chose to help him out so he could pull out with his protected and get a wildcard entry so he could save it for another tournament. "It gave me the win at the end". "In the moments when I probably needed to step it up, I did".
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He'll next face second-seeded defending champion Alexander Zverev of Germany, a 6-3, 6-2 victor over Russia's Daniil Medvedev.
Toronto's Daniel Nestor - the oldest player at the tournament at 45 - and Vancouver's Vasek Pospisil were scheduled to play their first-round doubles match in the late afternoon.
The tennis player further credited Tsitsipas for the victory and praised him for displaying commitment and discipline on the court.
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