I expect that this will be a short list. Here are the most legitimate candidates for greatest ever Canadian player. This is not an exhaustive list. 1) Lorne Main Current World #1 over 80 World #1 over 70 in 2000 Champion Monte Carlo clay 1954 Davis Cup 14 wins 14 defeats in singles 2) Bob Bedard Last Canadian to win the Canadian championship 1955, 1957, 1958 defeating in the finals Ramanathan Krishnan (World #3) and Whitney Reed (U.S.A. #1) Davis Cup greatest success in 1961, defeating both Llamas and Osuna (World #1) in singles Defeated Emerson (World #1) at Queens Club 1958 Won a set off Hoad at Wimbledon 1954, lost 3 matches to Hoad in Slam events (Roland Garros, Wimbledon, Forest Hills) lost to both Hoad and Rosewall in 1955 Davis Cup 3) Mike Belkin Rated #7 in world in early 1960's Davis Cup record 14 wins 7 defeats in singles 4) Daniel Nestor Defeated world #1 Edberg in five sets in 1992 Davis Cup singles Won numberless doubles titles, all four slam events and world titles 5) Greg Rusedski U.S. Open runnerup 1997 Ranked #4 in world Dual citizen, played Davis Cup for Britain 6) Milos Raonic Current world #14 Defeated Murray at Japan Open 2012 (career record 2 wins 1 defeat against Murray) 7) Filip Peliwo Current 2012 Wimbledon and U.S. Open Junior Champion World Junior #1 2012 Canada has not been a hotbed of tennis until recently, but the above is an honourable list. I would rate Bob Bedard as all-time number 1, but this could change if Raonic or Peliwo continue to develop.