Chiles Timberwolves (Leon county)
est 1999

1999 JV only
2000 6-4 HC Mike Hickman
2001 3-7 HC Mike Hickman
2002 2-7 HC Jodie Sprenkle
2003 6-4 HC Jodie Sprenkle
2004 2-8 HC Jodie Sprenkle
2005 6-4 HC Jodie Sprenkle
2006 6-4 HC Jodie Sprenkle
2007 5-4 HC Art Witters
2008 0-10 HC Art Witters
2009 5-5 HC Barney Myers
2010 2-8 HC Barney Myers
2011 6-4 (5-5) HC Mike Lassiter (forfeit win v Godby)
2012 3-7 HC Mike Lassiter
2013 3-6 HC Mike Lassiter
2014 1-9 HC Garrett Jahn
2015 6-5 HC Garrett Jahn District Runner-Up
2016 3-6 HC Garrett Jahn
2017 6-4 HC Kevin Pettis
2018 6-4 HC Kevin Pettis
2019 6-5 HC Kevin Pettis Wildcard 7 seed