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5 Most disappointing seasons in Cleveland Browns history

By Christopher Markoch

19 Nov 1995: Quarterback Vinny Testaverde of the Cleveland Browns starts to throw during the Browns 31-20 loss to the Green Bay Packers at Cleveland Stadium in Cleveland, Ohio. Mandatory Credit: Brian Bahr/Allsport
19 Nov 1995: Quarterback Vinny Testaverde of the Cleveland Browns starts to throw during the Browns 31-20 loss to the Green Bay Packers at Cleveland Stadium in Cleveland, Ohio. Mandatory Credit: Brian Bahr/Allsport /
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9 Aug 1999: A fan of the Cleveland Browns dresses up in a dog costume to show support of the Dog Pound during the Hall of Fame Game against the Dallas Cowboys at the Fawcett Stadium in Canton, Ohio. The Browns defeated the Cowboys 20-17.
9 Aug 1999: A fan of the Cleveland Browns dresses up in a dog costume to show support of the Dog Pound during the Hall of Fame Game against the Dallas Cowboys at the Fawcett Stadium in Canton, Ohio. The Browns defeated the Cowboys 20-17. /

The Cleveland Browns haven’t been great since returning to the NFL, but there was a time they had high expectations. Here we look over the 5 times they fell short of those lofty goals with the most disappointing seasons of all-time

What were the five most disappointing seasons in the storied history of the Cleveland Browns This is the question posed by Dawg Pound Daily’s Randy Gurzi to contributors Christopher Markoch and Elliot Kennel. Narrowing it down to only five disappointing seasons was difficult because there were several worthy contenders.

The nature of sports is that your team suffers excruciating defeats more often than they win it all. Only one team is truly happy at the end of the year, and everyone else’s season was disappointing in some sense.

Nevertheless, after much discussion, analysis (and probably a few beverages consumed) they came up with the following list, in order of emotional angst. While an entire generation of Browns fans has only known the Browns since the expansion era, we felt that it was important for fans to get a sense of the history of this iconic franchise. That meant we looked back over the time when they were a team that had lofty goals, which of course hurt much more when those goals were missed.

Therefore, the only post-1999 team to make the list was the 2017 winless wonders — although that did end in quite the parade, so that was something. Either way, we hope you enjoy this trip down memory lane — which starts with arguably the most iconic play in the team’s history.

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