It was double delight for the North American nation at Melbourne Park on Wednesday.
The Canadian began his tournament with a four-set win over his Serbian opponent.
The Canadian reaches the quarterfinals after beating the Russian in straight sets.
After suffering a surprise opening defeat, Canada managed to find their footing to keep its chance of winning their first Davis Cup title alive in Malaga.
The Russian overcame a rough start to clinch his second ATP trophy of the season.
Denis Shapovalov is into the quarter-finals in Stockholm.
The 23-year-old assured that five Canadians will compete in the second round after a tough five-set win against the Swiss qualifier.
Denis Shapovalov and Andy Murray exited Montreal while Nick Kyrgios and Grigor Dimitrov advanced.
Gilles Simon knocking out Pablo Carreno Busta was one of many upsets at Roland Garros on the men's side yesterday.
Denis Shapovalov has a lot thinking to do after his round one exit to Holger Rune in Paris.
The Canadian avenged a loss he suffered last year by beating the king of clay in the eternal city.
The Canadian needed three sets and over three hours to dispatch the Italian.
The Canadian was able to get by the Frenchman in straight sets in his opening match.
The Canadian was pushed to three sets by the Spaniard but was able to pull through.
The Czech qualifier managed to upset the Canadian in straight sets for his first win in an ATP main draw.
The two players give their versions about an argument which erupted during their clash at the Grand Slam.
The Spaniard was pushed to five sets but managed to pull a very tough win to reach the final four of the tournament.
Shapovalov's win ends his rivals bid to win his first Grand Slam and clinch the world No.1 ranking.
The Canadian managed to get past his 6ft 11 American opponent in a match that lasted over three hours.
Denis Shapovalov survived a tough test to reach the last 32 in Melbourne.