He played junior with three different Manitoba Junior Hockey League teams - the Winnipeg Rangers, St. James Canadians, and Winnipeg Monarchs. In 1940 he transferred to the junior and senior Toronto Marlboros. Dickens turned pro with the Providence Reds of the American Hockey League in 1941-42. The Toronto Maple Leafs called him up late in the season. He played with them through the playoffs and won the Stanley Cup. World War II then put his pro career on hold. He played for the senior Toronto RCAF Flyers team in 1942-43 and 1943-44.
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