The 17-year-old Canadian wildcard beat the Australian 11th seed 7-6 (7-2) 3-6 6-3 at the ATP 1000 event in Toronto.
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Shapovalov shocks Kyrgios at Rogers Cup in Toronto
Teenage world number 370 Denis Shapovalov stunned Nick Kyrgios in the Rogers Cup first round on Monday.
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Shapovalov, the Wimbledon junior champion, mixed 37 winners with 34 unforced errors in his surprise win.
Shapovalov broke in the second game of the deciding set on his way to a 3-0 lead he would not relinquish.
He will face Bulgarian Grigor Dimitrov in the second round.
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