Cole began broadcasting hockey on VOCM radio in St.John's NL. CBC Radio in 1969 and moved to television in 1973 when Hockey Night in Canada (HNIC) expanded its coverage. Cole was the primary play-by-play announcer for HNIC on CBC, usually working Toronto Maple Leafs games, from 1980 to 2008. Aside from the Leafs broadcasts, he was also a staple for HNIC during the annual Stanley Cup playoffs. He broadcast at least one game in every Stanley Cup Finals from 1980 until 2008, after which he was replaced by Jim Hughson. Until Rogers acquired the NHL rights, he had been HNIC's number two play-by-play man since 2008, primarily calling Montreal Canadiens games. His voice was also heard by a United States television audience whenever NBCSN simulcast an HNIC game that he was calling.
In November 2013, Rogers Communications reached a 12-year deal to become the exclusive national television and digital rightsholder for the NHL in Canada, beginning with the 2014–15 season. Although now at the age of 82, Cole told the Toronto Sun that he wanted Rogers to call and tell him if he would be a part of their hockey coverage: "I still feel the same as when I was 50. I still love what I'm doing. I just want to do games." Cole later stated, "I'd like to keep going. I feel good. I love the game. I still get passionate. I still get butterflies." In June 2014, Rogers confirmed that Cole would be part of their play-by-play team." Since then, he also does call selected games for Rogers Hometown Hockey, a Sunday night telecast airing on Sportsnet.
Cole's work during CBC's broadcasts of the Olympic games have also become memorable among legions of Canadians. His call on the final shot of the shootout in the semi-final game of the 1998 Winter Olympics at Nagano between Canada and the Czech Republic represented Canada's then-ongoing failure at the games and haunted fans for the next four years. With Canada scoreless in the shootout and Brendan Shanahan representing their last chance, Cole said in a panicked voice as Shanahan skated in towards Czech goalie Dominik Hasek, "He's gotta score, that's all!" But Shanahan was stopped by Hasek, prompting Cole to dejectedly say "No, he can't do it."
At the gold medal game of the 2002 Winter Olympics in Salt Lake City between Canada and the United States, Cole's animated call of Joe Sakic's second goal of the game is also one of his more memorable moments. Also, when Jarome Iginla scored Canada's fourth goal of the game, with four minutes remaining in the third period, Cole was so excited when the goal was scored he yelled out "GORE!" (a hybrid of "goal" and "score"), and then proceeded to call out "Goal, Canada! Goal! Wow! A lot of Canadian fans here! The place goes crazy here in Salt Lake City, and I guess coast to coast in Canada, and all around the world!" When Sakic scored Canada's fifth goal with one minute and twenty seconds remaining, Cole yelled out "Scores! Joe Sakic scores! And that makes it 5-2 Canada! Surely, that's gotta be it!" As the final seconds of the game ticked away, and as the crowd broke out in perfect unison singing O Canada, Cole said, "Now after 50 years, it's time for Canada to stand up and cheer. Stand up and cheer everybody! The Olympics Salt Lake City, 2002, men's ice hockey, gold medal: Canada!"
With an average Canadian audience of 10.6 million viewers, that game was the most-watched CBC Sports program, beating the previous record of 4.957 million viewers for Game 7 of the 1994 Stanley Cup Finals (the final game of the 1972 Summit Series between an NHL all-star team and the Soviet Union, which had been the most-watched sports program Canadian television history, was simulcast on CBC and CTV while Cole called the game on CBC Radio), in which the New York Rangers won their first Stanley Cup in 54 years, beating the Vancouver Canucks, another moment Cole himself called: "The New York Rangers have done it here on a hot June night in New York! The Rangers are Stanley Cup Champions!"
Cole's long time colour commentator on HNIC was Harry Neale. They were first teamed up in the 1986-87 season. From 1987 to 2008, they broadcast 21 Stanley Cup Finals together. Prior to that, his usual partners included Gary Dornhoefer, Mickey Redmond or John Davidson. Dick Irvin, Jr. also often joined his broadcast team as a third man in the booth for big games.
In 2007 Cole captured his first Gemini Award in the area of Sports Play-by Play.
Cole was inducted into the Hockey Hall of Fame in 1996 as the recipient of the Foster Hewitt Memorial Award for broadcasting excellence.
Prior to his career in broadcasting, Cole was a successful curler, playing in the 1971 and 1975 Briers as the skip for the Newfoundland team. He also played in the 1965 and 1973 Canadian mixed championship.
Cole received an honorary Doctorate of Laws from Memorial University of Newfoundland in St. John's in 2002.
In early 2016, Cole had a cameo at the end of Simple Plan's album Taking One for the Team, calling a fictional hockey game involving the band; he concluded the call with, "Oh my goodness, can you believe it? Just like that, Simple Plan have won the game!".
On September 23, 2016 Cole was appointed to the Order of Canada.