Currently (2011 season), the longest ever playoff losing streak is 7 straight games by the Kansas City Chiefs. They lost the 1993 AFC Championship game to the Bills, 1994 Wildcard to the Dolphins, 1995 Division to the Colts, 1997 Division to the Broncos, 2003 Division to the Colts, 2006 Wildcard to the Colts, and 2010 Wildcard to the Ravens.
Many teams have lost 6 straight including the Giants (1939-1950), Browns (1969-1985), Vikings (1988-1996), Cowboys (1996-2007), Lions (1991-1999) and Seahawks (1984-2004). The Lions streak is current as they have not made the playoffs since 1999 when the lost to the Redskins in a Wildcard game.
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Through the 2008 season, that distinction is held jointly by the Buffalo Bills and Detroit Lions whose last playoff appearance was in the 1999 season.
The New Orleans Saints.
barry sanders did it for over 10 years.
No.
Yes. For ten years, 1960-1969, the NFL played a game called the Playoff Bowl that pitted the two losing teams from the playoffs (only four teams made the playoffs at the time). The game was played the week following the NFL Championship game. Six of these games were played before the Super Bowl was created ... four after. The Playoff Bowl games ended with the AFL-NFL merger.