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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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Q: What is the longest playoff losing streak in the NFL?
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