In 1968, the Winnipeg Blue Bombers made their first CFL postseason appearance in twelve years, taking on the Calgary Stampeders in the first round of the 1968 CFL Western Division playoffs. The Blue Bombers took a 13-0 lead in the first half only to collapse early in the second half and lose to Calgary 34-20.

The Stampeders subsequently beat Saskatchewan in the Western Division finals and were in turn defeated by the Eastern Division champion Ottawa Rough Riders in the 1968 Grey Cup title game in a 13-12 nailbiter. As for Winnipeg, its inglorious first round exit at Calgary's hands would mark the first of four straight early eliminations for the Bombers in the late '60s and early '70s.