The Whitby Dunlops were originally founded in 1954 when the 1952/53 Oshawa Generals were disbanded after their arena burned down. Some of the players, along with coach and manager, Wren Blair, formed the Oshawa Truckmen for the 1953/54 season. In 1954, the Oshawa Truckmen relocated to Whitby and were temporarily renamed the Whitby Seniors.

The team played out of the Whitby Community Arena and were soon sponsored by the Dunlop Rubber Company. The newly renamed Whitby Dunlops started their first year as an Ontario Hockey Association Senior B team. After winning the league, they were promoted to the OHA Senior A League. The Whitby Senior Hockey Club was the executive committee that oversaw the operation and administration of the Whitby Dunlops hockey team.

The Whitby Dunlops won the league’s Allan Cup in both 1957 and 1959, the top prize for the OHA Senior A League. They also won the gold medal at the World Ice Hockey Championships in 1958 in Oslo, Norway. For all their victories, the Town of Whitby and Ontario County were extremely proud of the hockey team.

The members of the Whitby Dunlops were inducted into the Whitby Sports Hall of Fame in 1998. Notable members of the original Whitby Dunlops include former Whitby Mayor, Bob Attersley, former Toronto Maple Leafs captain Sid Smith, and Harry Sinden, former coach and general manager of the Boston Bruins.