The college formerly operated a junior ice hockey team from the 1910s to 1940s in the Ontario Hockey Association. The College won the J. Ross Robertson Cup as the playoffs champions in 1918.[15] Alumni from the junior hockey team who later played in the National Hockey League include, Babe Dye, Red Green, Jack Ingoldsby, Duke McCurry, Eddie Rodden, Sid Smith and Jesse Spring.[16]
De La Salle "Oaklands" have won multiple city and provincial championships (particularly in hockey and football) in the 1950s, 1960s, 1970s and 1980s. After the school had re-privatized in 1994, its initial efforts on the competitive playing fields were pale in comparison to its rich history. However, by the year 2000, teams from De La Salle were beginning to be noticed. Teams such as the Girls and Boys Varsity Hockey, Boys Varsity Basketball, Girls Volleyball, and Girls Soccer were regularly advancing far into the playoffs of their respective leagues, with some making their way to the OFSAA championships.
Notable alumni
Carl Brewer, NHL Defenceman Toronto Maple Leafs 1958–1980
Red Green, '18, NHL Forward 1923–1929
Kris Draper, '90, NHL Forward Detroit Red Wings 1990 to 2011
John D'Amico, NHL Referee / Linesman, Member Hockey Hall of Fame, 1937–2005
Rishi Ganjoo, '91, frontman of the Toronto-based rock trio Danko Jones
Jamal Mayers, NHL Forward St. Louis Blues, 1996–2007 Toronto Maple Leafs 2008, Calgary Flames 2010, Chicago Blackhawks 2011–2013
Dennis O'Connor, Associate Chief Justice – Ontario Superior Court of Justice, Judge – Court of Appeal for Ontario
Dennis T. O'Connor, Archbishop of Toronto 1899–1908
Richard Park, '94, NHL Forward New York Islanders 1994–1996, Anaheim Ducks 1997–1998, Philadelphia Flyers 1999, Minnesota Wild 2001–2004, Vancouver Canucks 2005, New York Islanders 2006–2010, Pittsburgh Penguins 2012
Keanu Reeves, actor
