9. Cincinnati Bengals (1988)
Football is a cruel sport as the Bengals discovered in this game. It may seem harsh to call this one of the biggest choke jobs in history. That’s a fair point because the 49ers had Joe Montana as their starting quarterback. However, given the context of the Bengals’ next 30 years, they wasted the chance to become iconic. Instead, they missed their only shot at the title.
It was an intriguing match-up because Boomer Esiason was in the best form of his life. This was a tight game and the Bengals led 16-13 with three minutes ticking away. However, they were unable to hold on as Joe Montana led his team downfield. The result was inevitable. Within a couple of years, Cincinnati was in severe decline. Finally, in 2022, they appeared in a Super Bowl again (via Mercury News).