Ranking Steelers last five playoff losses in order of pain and misery

The Pittsburgh Steelers have not won a playoff game since 2016, an embarrassing streak for an organization with a legendary history of winning in big moments.

2024-25: Steelers vs Ravens 

After a promising 10-3 start to the year, the Steelers dropped five games in a row, including their fourth-straight first round playoff exit. Their arch-rivals, the Baltimore Ravens, are clearly the better team right now, but this rates relatively low on the list of most painful losses because the four games leading up to it set fan expectations. 

2021-22: Steelers vs Chiefs

The Steelers barely managed a playoff appearance in 2021 with a 9-7-1 record, and the negative result against the eventual AFC champion Kansas City was no surprise. This loss could have been considered relatively painless if it were not Big Ben Roethlisberger’s last game in the black and yellow. However, the real late-career playoff tragedy for Ben came one year prior.

2016-17: Steelers vs Patriots

In 2016 the Steelers won the AFC North and their first two playoff games on the strength of the ‘Killer Bees.’ However, Le’Veon Bell’s injury in conference round neutered Pittsburgh’s offense after he had set rushing records in the two earlier wins that postseason, leading to another unceremonious exit at the hands of New England Tom Brady. 

2017-18: Steelers vs Jaguars

The 2017 Steelers appeared ready to right the wrongs of the year before, with a third-ranked offense and fifth-ranked defense in yardage. Yet they allowed 21 points in the first 19 minutes to a Jacksonville team making its first playoff appearance in ten years, and 42 points was not enough for Pittsburgh to catch up. 

2020-21: Steelers vs Browns

After starting the COVID-19 season with an 11-0 record, the Steelers limped into the playoffs at 12-4, slightly stronger than they did in 2024. Yet the scene that Pittsburghers were left with after that season, Ben Roethlisberger and his retiring center Maurkice Pouncey saying goodbye after a third consecutive playoff loss. The fact that it was the Browns – a team who the Steelers historical dominate – who embarrassed them made it that much worse, the most painful and tragic playoff loss in recent Pittsburgh sports memory.