Darryl Sly’s hockey career began with the Toronto St. Michael’s of the Ontario Hockey Association from 1956 through 1959, playing defense, before switching to the Galt Terriers of the league’s Senior A level for the 1960-1961 season. His hockey career, however, was taking off in all different directions: he was also recruited by Western International Hockey League’s Trail Smoke Eaters in preparation for the 1961 ice hockey World Championships, and also by the Kitchener-Waterloo Dutchmen to join Canada’s team at the 1960 Winter Olympics. At the Olympics, he played in seven games, scored one goal, and took home a silver medal. At the World Championships his team fared even better, taking home the gold medal as a member of the last amateur team ever to defeat the Soviets in an international tournament. He then spent several years, from 1960 through 1968, in the American Hockey League with the Rochester Americans, but also began a career in the National Hockey League with the Toronto Maple Leafs, playing two games with them in the 1965-1966 season. He played an additional 17 games with the team in the 1967-68 season before joining the Vancouver Canucks for the 1968-1969 season while they were still part of the now-defunct Western Hockey League. He moved to the NHL’s Minnesota North Stars in 1969, while also playing ten games for the Central Hockey League’s Iowa Stars in their only season with the league. He rejoined the Canucks (now a part of the NHL) and the Americans the following year, in what would be his final year in the NHL. He played two more seasons with the Americans, and seven more with the Ontario Hockey Association’s senior level Barrie Flyers, before retiring from playing hockey in 1978.
Sly coached the Flyers from 1971-1973, and again in the 1975-1976 season, but did not retire from coaching until 1987, the year his Collingwood Shipbuilders took the Ontario Hockey Association’s Senior “A” championship. He was inducted into the Rochester Americans Hall of Fame in 1986. Outside of hockey, he taught school, developed real estate and successfully owned and managed Blue Mountain Chrysler in Collingwood, the city where he died of cancer in 2007.
Canada