Someday....someday I'll be the head coach at Red Boiling Springs and people will forget that they were ever mentioned on this thread.
In Ohio, there's a couple of brutal ones. Grove City HS had some real good teams in the late 1990s until a new high school (Central Crossing) was built. Grove City hasn't done jack since, but Central Crossing is hideously bad. Their records since the team started have been:
2008 -- 1-9
2007 -- 1-9
2006 -- 2-8
2005 -- 2-8
2004 -- 2-8
2003 -- 3-7
2002 -- 0-10
Overall -- 9-61
Probably the worst, though, is Sebring McKinley.
2008 -- 0-10
2007 -- 1-9
2006 -- 0-10
2005 -- 1-9
2004 -- 1-9
2003 -- 1-9
2002 -- 0-10
2001 -- 0-9
2000 -- 0-10
Overall this decade -- 4-75
W-L record of the teams that they've beaten -- 3-36
Funny thing is that my uncle is a McKinley grad, and last year he asked me about how their team was (since he lives in Michigan now). I said, "Oh, I think they're 3-67 this decade." Without batting an eye, he said, "Well, I guess some things never change."