"It's a dream of any kid out there in this world, any kid that's playing tennis, to beat these kinds of players, so I can call it the best moment of my life", a shocked Tsitsipas said on Thursday.
Djokovic was chasing his fifth Rogers Cup title but was beaten in three sets by Tsitsipas, who turns 20 this weekend.
Buoyed by an enthusiastic crowd on the smaller venue, Shapovalov advanced to the third round of the Rogers Cup by defeating the 14th-seeded Italian 6-3, 7-5 in a match that was delayed for hours and interrupted in the first set by heavy rains. "I knew I was playing pretty good today".
Auger-Aliassime was coming off the biggest win of his career, downing No. 18 Lucas Pouille of France in straight sets on centre court on Tuesday.
'It was a good match, a very positive victory for me over a tough opponent, ' Nadal said.
Djokovic said he was having no problems with the shot clock despite being a player who regularly picks up violations for the length of time he takes between points. "So just all in all, it wasn't that great of a match".
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).
The big-serving sixth-ranked South African hit 15 aces and won 86 per cent of first serves in en route to the 7-5 6-3 victory.
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Del Potro, who had a bye in the first round after reaching the Los Cabos final last week, was set to play Robin Haase of the Netherlands.
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.
"Sorry to my fans in Toronto, but I have to pull out of the tournament since my left wrist needs some days of rest", Del Potro said in a tweet.
Djokovic has been stunned by the teenager Tsitsipas in Toronto. "It gave me the win at the end".
However, Tsitsipas did well to break Djokovic for a 2-0 lead in the third set and never looked back.
Nadal was made to work harder in the second where the players exchanged breaks over six consecutive games before the world number one finally held in the ninth to seal the match when Paire sent a service return wide.
Nick Kyrgios has lost to former world No.3 and one-time sparring partner Stan Wawrinka in the opening round of the ATP Masters 1000 event in Canada. He'll next face second-seeded defending champion Alexander Zverev of Germany, a 6-3, 6-2 victor over Russia's Daniil Medvedev.
They beat French duo Pierre-Hugues Herbert and Nicolas Mahut 4-6, 6-4, 10-7.