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It depends on how you define a team. The Saskatchewan Roughriders, formerly Regina Roughriders, have lost 15 Grey Cup Games. The Hamilton Tiger-Cats and their predecessor teams the Tigers and Wildcats (whose victories are always counted with Hamilton's) have also lost a total of 15. Winnipeg Blue Bombers have lost the game 14 times, but if you count the two losses by the Winnipeg RCAF team during the war, that makes 16.

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