The Winnipeg Blue Bombers have won 10 Grey Cups in total. They won the championship in each of the following years: 1935, 1939, 1941, 1958, 1959, 1961, 1962, 1984, 1988, and 1990. For scores follow this link: http://www.bluebombers.com/page/grey_cups The Winnipeg Blue Bombers also have the most Grey Cup appearances of any team at 23.
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10 championships from 23 appearances. Most appearances of any team, 3rd most wins behind Toronto (16) and Edmonton (13)
Zero, There were only 3 Grey Cups played in Winnipeg and the Bombers were not in any of them.
Ten as stated in the Winnipeg Blue Bombers Wiki
Grey Cup wins 1935, 1939, 1941, 1958, 1959, 1961, 1962, 1984, 1988, 1990