Their longest is 8
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Currently... The Detroit Red Wings (20 years straight and continuing).
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.
Mickey Mantle's longest hitting streak was 16 games.
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 Boston Bruins' longest streak was 14 games from December 3, 1929 to January 9, 1930