#2 Milos Raonic
Monaco resident Milos Raonic is the highest ever ranked Canadian tennis player in the singles category. He achieved a career-high ranking of World Number 3 in November 2016.
Raonic has been a consistent performer at the ATP level for almost six years. With about $17.5 million in prize money, he is already ranked inside the top 25 highest prize-money earners of all time.
One of the most dominant servers on tour, Raonic has won a whopping 91% of the service games in his career. The 6'5" Canadian is currently coached by former Wimbledon champion Goran Ivanisevic.
Raonic's career highlight till date has been his performance at the Wimbledon Championships of 2016 where he beat Roger Federer in the semifinals. He would eventually finish runner-up to home favorite Andy Murray.
All eight of Raonic's ATP title wins have come on hard courts, with a pair each at the Chennai Open and the San Jose Open.