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The CFL was formed in 1958. Since then Hamilton has lost 11 times, Edmonton and Montréal 8, Saskatchewan 7, Winnipeg and Calgary 6, BC 4, and Toronto 3.

If you include Grey Cup losses before 1958, Saskatchewan lost a further 8 games (total 15), Winnipeg also a further 8 (total 14), Toronto 3 (total 6), Montréal 3 (total 11), Calgary 1 (total 7), and Edmonton 1 (total 9).

If you include two losses by Winnipeg RCAF teams that makes 16 for them. Hamilton Tiger Cats did not lose any Grey Cup games before 1958, but Ticat fans like to count the Grey Cup victories of their predecessor teams the Tigers and the Wildcats, so to be fair one ought to count the three losses by the Tigers and the one by the Wildcats, giving Hamilton a total of 15 like Saskatchewan.

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Q: Which CFL team lost 15 grey cup games?
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