| 2020 |
| Fri., Nov. 6 | @ Fayette Ware | W 27-24 | 1st Round Playoffs | | Fri., Nov. 13 | @ Ripley | L 21-36 | 2nd Round Playoffs |
| 2019 |
| Fri., Nov. 8 | vs. Bolton | W 56-0 | 1st Round Playoffs | | Fri., Nov. 15 | @ Millington | W 70-35 | 2nd Round Playoffs | | Fri., Nov. 22 | @ Haywood | L 35-41 | 3rd Round Playoffs |
| 2018 |
| Fri., Nov. 2 | @ Craigmont | W 48-12 | 1st Round Playoffs | | Fri., Nov. 9 | @ Dyersburg | L 12-28 | 2nd Round Playoffs |
| 2017 |
| Fri., Nov. 3 | vs. Fayette Ware | W 56-18 | 1st Round Playoffs | | Fri., Nov. 10 | vs. Dyersburg | W 47-20 | 2nd Round Playoffs | | Fri., Nov. 17 | @ Haywood | L 21-49 | 3rd Round Playoffs |
| 2014 |
| Fri., Nov. 7 | vs. Raleigh Egypt | W 69-27 | 1st Round Playoffs | | Fri., Nov. 14 | vs. Jackson North Side | W 35-6 | 2nd Round Playoffs | | Fri., Nov. 21 | vs. Trezevant | L 17-20 | 3rd Round Playoffs |
| 2013 |
| Fri., Nov. 8 | @ Dyersburg | L 7-28 | 1st Round Playoffs |
| 2012 |
| Fri., Nov. 2 | @ Maplewood | L 3-15 | 1st Round Playoffs |
| 2010 |
| | Kingsbury | L 19-35 | 1st Round Playoffs |
| 2009 |
| | Kingsbury | W 34-14 | 1st Round Playoffs | | | Sheffield | W 30-12 | 2nd Round Playoffs | | | Liberty Tech | L 28-31 | 3rd Round Playoffs |
| 2008 |
| | Mitchell | L 20-40 | 1st Round Playoffs |
| 2006 |
| | Frayser | W 56-0 | 1st Round Playoffs | | | Covington | L 28-33 | 2nd Round Playoffs |
| 2005 |
| | Mitchell | W 22-21 | 1st Round Playoffs | | | Sheffield | W 24-14 | 2nd Round Playoffs | | | Covington | L 7-25 | 3rd Round Playoffs |
| 2004 |
| | Page | W 10-3 | 1st Round Playoffs | | | Jackson South Side | L 17-28 | 2nd Round Playoffs |
| 2003 |
| | Marshall County | W 42-7 | 1st Round Playoffs | | | Page | W 28-24 | 2nd Round Playoffs | | | Greenbrier | L 13-20 | 3rd Round Playoffs |
| 2002 |
| | Cheatham County | W 49-21 | 1st Round Playoffs | | | Greenbrier | W 21-20 | 2nd Round Playoffs | | | Marshall County | W 45-0 | 3rd Round Playoffs | | | Ridgeway | L 0-29 | Semi-finals Playoffs |
| 2001 |
| | Page | W 26-23 | 1st Round Playoffs | | | Jackson South Side | W 9-7 | 2nd Round Playoffs | | | Sycamore | W 9-7 | 3rd Round Playoffs | | | Covington | W 16-3 | Semi-finals Playoffs | | | Austin-East | L 17-27 | Championship Game |
| 2000 |
| | Giles County | W 35-0 | 1st Round Playoffs | | | Marshall County | L 13-16 | 2nd Round Playoffs |
| 1999 |
| | Marshall County | W 30-14 | 1st Round Playoffs | | | Milan | L 7-45 | 2nd Round Playoffs |
| 1998 |
| | Frayser | L 0-6 | 1st Round Playoffs |
| 1997 |
| | Frayser | W 40-21 | 1st Round Playoffs | | | Melrose | L 7-45 | 2nd Round Playoffs |
|
| Crockett County Playoff Totals |
| Record |
26-20-0 1226-950 |
| Home Record | 5-1 |
| Away Record | 3-6 |
|
