The battle of the two Canadians didn't go as planned...
The Canadian is through to his first quarter-final on the Tour since Wimbledon.
Denis Shapovalov eased into the last 32 at the US Open.
Denis Shapovalov cruised into the second round at the US Open.
Novak Djokovic defeated a valiant Denis Shapovalov to reach the Wimbledon final.
Can the 22-year-old spring a massive upset at The All England Club on Friday?
Shapovalov has the tools to trouble Djokovic, while Hurkacz beats Federer and looks born to play on grass
Denis Shapovalov reached the Wimbledon semi-finals with a five set victory over Karen Khachanov.
Denis Shapovalov cruised past Andy Murray to reach the second week at Wimbledon.
Denis Shapovalov needed five sets to progress to the second round at Wimbledon.
It will be the first time Shapovalov has missed a Grand Slam main draw since 2017.
Casper Ruud won his second career ATP title in Geneva.
Denis Shapovalov reached his third career ATP Final in Geneva.
Denis Shapovalov battled past Marco Cecchinato to reach the Geneva quarter-finals.
Rafael Nadal saved match points to edge out Denis Shapovalov in Rome.
The Canadian number 11 seed only needed 62 minutes to dispatch his Serbian opponent.
Corentin Moutet beats Denis Shapovalov in an epic match in Estoril.
The world No.14 spoke about a variety of topics in Portugal ahead of his next campaign on the Tour.
The Canadian kept his perfect record alive against the Frenchman.
The Canadian survived a three set marathon and a rain delay to beat the Belorussian.