Four-time champion Novak Djokovic crashed out of the Rogers Cup in the third round as Stefanos Tsitsipas claimed a deserved 6-3, 6-7 (5-7), 6-3 triumph.
The former world number one did not look himself early on and Tsitsipas took full advantage, but the tide appeared to be turning on the 19-year-old when he was pegged back in a second-set tie-break.
However, Tsitsipas kicked on again to take control of the decider and complete an upset, sending the Wimbledon champion out in sensational fashion.
Djokovic was made to work to hold in his first service game and a laboured start soon handed Tsitsipas the break, the Serbian going long and then, failing to recover and rescue the opener.
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The favourite was much improved in the second set, but still could not shake off Tsitsipas, needing to save two late break points as his opponent closed on victory.
But, Djokovic quickly built a lead in the tie-break and, although Tsitsipas threatened a fightback with further measured returns, the gap proved too great to bridge, taking the match to a decider with his third set point.
Tsitsipas would not be brushed aside, though, and a huge shot down the line sealed an early break in the third, before fighting back in a sublime hold that prompted Djokovic to smash his racket.
There was to be no reprieve and Tsitsipas was ultimately comfortable as he allowed Djokovic to hold and pressed home the advantage on his own serve to seal victory.
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