The lanky wild card kissed the Montreal court after completing a rousing 3-6 6-4 7-6(4) triumph as the 18-year-old became the youngest player to ever reach the quarter-finals of an ATP Masters 1000 event.
Federer through to Rogers Cup final
The early exit also denied world number two Nadal a chance to take over from the absent Andy Murray at the top of the rankings, a position the Spaniard would have regained for the first time since 2014 had he advanced to the semi-finals.
Denis Shapovalov, après sa victoire sur Rafael Nadal, au Masters 1000 de Montréal.
Image credit: Getty Images
Shapovalov showed no sign of nerves in their first ever meeting, the left-hander playing the more aggressive tennis by utilising his huge forehand on roundhouse swings and frequently attacking the net.
The teenager's quixotic bid looked doomed in the third set tiebreaker when he fell 3-0 behind but the world number 143 refused to buckle and only coughed up one more point in the decider.
As a reward for his unlikely victory, the 2016 Wimbledon junior champion will next face 29-year-old Frenchman Adrian Mannarino in the quarter-finals on Friday.
Next up for Roger Federer is a quarter-final against 12th-seeded Spaniard Roberto Bautista Agut, who defeated Frenchman Gael Monfils 4-6 7-6(5) 7-6(2) in a marathon tussle.
In other tournament action, American Jared Donaldson lost to Diego Schwartzman 0-6 7-5 7-5, while his countryman Sam Querrey was thrashed 6-4 6-1 by Kevin Anderson of South Africa.
Australian Nick Kyrgios fell 6-4 6-3 to fourth seed Alexander Zverev as the German finally claimed victory over his opponent in their third meeting of the season.
Results from the Montreal Masters Men's Singles Round 3 matches on Thursday
- Denis Shapovalov (Canada) beat 1-Rafa Nadal (Spain) 3-6 6-4 7-6(4)
- Adrian Mannarino (France) beat Chung Hyeon (South Korea) 6-3 6-3
- 4-Alexander Zverev (Germany) beat 16-Nick Kyrgios (Australia) 6-4 6-3
- 2-Roger Federer (Switzerland) beat David Ferrer (Spain) 4-6 6-4 6-2
- Robin Haase (Netherlands) beat 7-Grigor Dimitrov (Bulgaria) 7-6(3) 4-6 6-1
- 12-Roberto Bautista (Spain) beat Gael Monfils (France) 4-6 7-6(5) 7-6(2)
- Diego Schwartzman (Argentina) beat Jared Donaldson (U.S.) 0-6 7-5 7-5
- Kevin Anderson (South Africa) beat Sam Querrey (U.S.) 6-4 6-1
Federer cruises to semi-finals in Montreal
Federer loses set streak but bounces back to beat Ferrer
Share this article