The 29 most hopeless fan bases in professional sports

CLEVELAND, OH - DECEMBER 13, 2015: Cleveland Browns fans hold up signs reading 'HELP' during a game against the San Francisco 49ers on December 13, 2015 at FirstEnergy Stadium in Cleveland, Ohio. Cleveland won 24-10. (Photo by Nick Cammett/Diamond Images/Getty Images) /

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LOS ANGELES, CA: Jim Kelly of the Buffalo Bills circa 1988 drops back to pass against the Los Angeles Radiers at the Coliseum in Los Angeles, California. (Photo by Owen C. Shaw/Getty Images) /

5. Buffalo Bills

Last championship: 1965 (AFL championship)

Last winning season: 2014

It’s been brought up already throughout this countdown, but sometimes it’s hard to say what’s worse: the pain of being a perpetual bottom feeder, or the pain in known the heights of competition, only to be continually knocked down from them.

This is the story of the Buffalo Bills, the only franchise in history to lose four consecutive Super Bowls. They won 49 regular season games from 1990 through 93 and blew out several opponents throughout the AFC playoff bracket, only to be brought to a knee by continually in each Super Bowl. That’s the ultimate Groundhog Day in the world of sports.

And what has followed has been another sort of scuffle that is becoming equally confounding. The Bills have not made the playoffs since 1999, the longest standing streak in the game. This has spanned eight coaches, 11 quarterbacks, the death of long-time owner Ralph Wilson, and franchise hero Jim Kelly’s bout with cancer.

It takes a certain type of resiliency as it is to get up and brave the cold of a Buffalo winter to watch football. So to be met with this type of continuous frustration, with losing outcomes of every variety, says that perhaps no fans in football are more due for a break than those of the Bills.

Next: 4. Toronto Maple Leafs