| 2018 |
| Sat., Nov. 3 | @ Springfield | L 12-47 | 1st Round Playoffs |
| 2017 |
| Fri., Nov. 3 | @ White House | L 26-36 | 1st Round Playoffs |
| 2014 |
| Fri., Nov. 7 | vs. Jackson North Side | L 7-14 | 1st Round Playoffs |
| 2013 |
| Fri., Nov. 8 | @ Giles County | L 14-47 | 1st Round Playoffs |
| 2012 |
| Sat., Nov. 3 | @ White House | L 10-24 | 1st Round Playoffs |
| 2011 |
| | Kingsbury | W 49-15 | 1st Round Playoffs | | | Mitchell | W 28-14 | 2nd Round Playoffs | | | Covington | L 19-33 | 3rd Round Playoffs |
| 2010 |
| | Greenbrier | L 7-12 | 1st Round Playoffs |
| 2009 |
| | Giles County | L 20-45 | 1st Round Playoffs |
| 2008 |
| | David Lipscomb | L 14-48 | 1st Round Playoffs |
| 2005 |
| | David Lipscomb | L 12-48 | 1st Round Playoffs |
| 2003 |
| | Fairview | W 35-8 | 1st Round Playoffs | | | Huntingdon | L 0-47 | 2nd Round Playoffs |
| 1998 |
| | Spring Hill | L 14-33 | 1st Round Playoffs |
| 1997 |
| | Spring Hill | L 13-28 | 1st Round Playoffs |
| 1994 |
| | Kingsbury | L 14-48 | 1st Round Playoffs |
| 1993 |
| | Ridgeway | L 12-17 | 1st Round Playoffs |
|
| Chester County Playoff Totals |
| Record |
3-15-0 306-564 |
| Home Record | 0-1 |
| Away Record | 0-4 |
|
