Sinden played defence for the Toronto Marlboro bantams before moving up to the Oshawa Generals of the Ontario Hockey Association\n', ' for junior hockey. He played in Oshawa from 1949 to 1953, and then for six seasons in the OHA senior division with the Whitby Dunlops. He was team captain when the Dunlops won the Allan Cup in 1957, and then the 1958 World Hockey Championship for Canada in Oslo, Norway. He also won a silver medal as a member of the Canadian national men\'s hockey team at the 1960 Winter Olympics\n', ' in Squaw Valley, California. The core of the team was the Kitchener-Waterloo Dutchmen, with Sinden one of four players from the Dunlops added to the lineup to strengthen the team for the Olympics.\n', '

Near the end of the season, the Montreal Canadiens placed Sinden on their negotiation list but didn\'t reach an agreement with him. After playing some games with the Hull-Ottawa Canadiens in the Eastern Professional Hockey League he met Lynn Patrick, general manager of the Boston Bruins, who signed him as player – assistant coach for the Kingston Frontenacs, the Bruins\' EPHL affiliate, starting in 1960–61. He was named a first-team all-star for the 1961–62 season and league MVP for 1962–63. After the league folded, the team became the Minneapolis Bruins of the Central Hockey League for the 1963–64 season with Sinden as player-coach. After two seasons the team moved again, becoming the Oklahoma City Blazers, where Sinden finished his playing career in 1965–66 after six seasons with the franchise. In that final season, he coached the team to the league championship.\n', '

In May 1966, Sinden moved up to the NHL as head coach of the Boston Bruins. At 33 he was the youngest coach in the league at the time, coaching the youngest team. In his first season — with a team that included rookie Bobby Orr—the Bruins finished out of the playoffs with the worst record in the league. But in his second year, aided by the acquisition of Phil Esposito from the Chicago Black Hawks, the team posted a winning record; and in his third season, the Bruins finished with 100 points just behind the Montreal Canadiens for top spot in the NHL. In his fourth season, 1969–70, he coached the Bruins to their first Stanley Cup in 29 years.\n', '

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