I'm sticking with my mighty Red Boiling Springs Bulldogs

...
50-328 All-time (started 1974)
69-game losing streak from 1986-1992
61-game losing streak from 2002-2009
1 winning season in 39 years of play
0 playoff appearances in 39 years of play
60-point+ defeats all-time
2005 L Trousdale County 91-0
1976 L Gordonsville 76-0
2010 L Friendship Christian 72-0
2007 L Watertown 76-7
2007 L Friendship Christian 65-0
1989 L Westmoreland 65-0
1975 L Spring Hill 65-0
1974 L Clay County 76-12
1996 L Trousdale County 62-0
2006 L Friendship Christian 61-0
2000 L Gordonsville 69-8
2009 L Friendship Christian 60-0
2004 L East Robertson 60-0
1997 L Trousdale County 60-0
1988 L Watertown 60-0
1975 L Watertown 60-0