The nine-year playoff streak is masking a two-year playoff win drought

Winnipeg has made the postseason nine consecutive seasons with five Grey Cup appearances and two titles in that span, but the last playoff victory came in the 2024 West Final against Saskatchewan. In 2025 they missed the championship game for the first time in six years, losing the East Semi-Final to Montreal as a crossover team — and they enter Week 20 at 8-8, needing a win or a Calgary loss to avoid being the West's fourth seed again.