| 2018 |
| Sat., Nov. 3 | @ Pearl-Cohn | L 7-47 | 1st Round Playoffs |
| 2017 |
| Fri., Nov. 3 | vs. East Nashville | L 3-13 | 1st Round Playoffs |
| 2016 |
| Fri., Nov. 4 | @ Stratford | L 6-42 | 1st Round Playoffs |
| 2015 |
| Fri., Nov. 6 | @ CPA | L 0-41 | 1st Round Playoffs |
| 2012 |
| Fri., Nov. 2 | vs. Grundy County | W 69-30 | 1st Round Playoffs | | Fri., Nov. 9 | vs. Fairview | W 36-21 | 2nd Round Playoffs | | Fri., Nov. 16 | vs. CPA | L 21-37 | 3rd Round Playoffs |
| 2011 |
| | CPA | L 7-17 | 1st Round Playoffs |
| 2007 |
| | Fayette Ware | L 28-34 | 1st Round Playoffs |
| 2006 |
| | Jackson South Side | L 35-42 | 1st Round Playoffs |
| 2005 |
| | Liberty Tech | W 20-9 | 1st Round Playoffs | | | David Lipscomb | L 3-13 | 2nd Round Playoffs |
| 2004 |
| | McKenzie | W 50-28 | 1st Round Playoffs | | | Huntingdon | L 0-14 | 2nd Round Playoffs |
| 2003 |
| | McKenzie | L 24-34 | 1st Round Playoffs |
| 2002 |
| | Crockett County | L 21-49 | 1st Round Playoffs |
| 1997 |
| | Tullahoma | L 6-17 | 1st Round Playoffs |
| 1995 |
| | Hardin County | W 27-14 | 1st Round Playoffs | | | Westwood | L 13-27 | 2nd Round Playoffs |
| 1994 |
| | Lexington | W 48-20 | 1st Round Playoffs | | | Westwood | L 7-13 | 2nd Round Playoffs |
| 1988 |
| | Brentwood Academy | L 7-43 | 1st Round Playoffs |
| 1987 |
| | Brentwood Academy | L 7-42 | 1st Round Playoffs |
|
| Cheatham County Playoff Totals |
| Record |
6-17-0 445-647 |
| Home Record | 2-2 |
| Away Record | 0-3 |
|
